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157764-10-8

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157764-10-8 Usage

Description

2-[3-Chloro-5-(trifluoroMethyl)-2-pyridinyl]-acetonitrile is an organic compound characterized by its unique molecular structure, which features a chloro and trifluoromethyl group attached to a pyridine ring, with an acetonitrile group at the 2nd position. 2-[3-Chloro-5-(trifluoroMethyl)-2-pyridinyl]-acetonitrile is known for its potential applications in the pharmaceutical industry due to its chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
2-[3-Chloro-5-(trifluoroMethyl)-2-pyridinyl]-acetonitrile is used as a key intermediate in the synthesis of various pharmaceutical compounds, specifically for the preparation of (pyridyl)pyrazolopyrimidines. These compounds serve as corticotropin-releasing factor (CRF) receptor antagonists, which have potential therapeutic applications in treating stress-related disorders, anxiety, and depression.
The compound's unique structure allows for the development of CRF receptor antagonists that can modulate the stress response system, providing a new avenue for the treatment of various conditions related to stress and anxiety. By targeting the CRF receptors, these antagonists can help regulate the body's response to stress and potentially alleviate the symptoms associated with stress-related disorders.

Check Digit Verification of cas no

The CAS Registry Mumber 157764-10-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,7,7,6 and 4 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 157764-10:
(8*1)+(7*5)+(6*7)+(5*7)+(4*6)+(3*4)+(2*1)+(1*0)=158
158 % 10 = 8
So 157764-10-8 is a valid CAS Registry Number.

157764-10-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]acetonitrile

1.2 Other means of identification

Product number -
Other names 3-chloro-5-trifluoromethyl pyridine-2-acetonitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:157764-10-8 SDS

157764-10-8Synthetic route

2,3-dichloro-5-trifluoromethylpyridine
69045-84-7

2,3-dichloro-5-trifluoromethylpyridine

acetonitrile
75-05-8

acetonitrile

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

Conditions
ConditionsYield
With sodium methylate at 130℃; under 21002.1 Torr; for 16h; Pressure; Temperature; Reagent/catalyst; Inert atmosphere;99.2%
2,3-dichloro-5-trifluoromethylpyridine
69045-84-7

2,3-dichloro-5-trifluoromethylpyridine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

Conditions
ConditionsYield
Stage #1: 2,3-dichloro-5-trifluoromethylpyridine; ethyl 2-cyanoacetate With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 70℃; for 3h;
Stage #2: With hydrogenchloride In 1-methyl-pyrrolidin-2-one; water at 130℃; for 2h; pH=2;
94%
Stage #1: ethyl 2-cyanoacetate With 18-crown-6 ether; potassium carbonate In ethyl acetate at 25℃; for 0.5h;
Stage #2: 2,3-dichloro-5-trifluoromethylpyridine In ethyl acetate at 70℃; for 1h;
Stage #3: With hydrogenchloride In N,N-dimethyl-formamide for 3h; pH=2; Reagent/catalyst; Solvent; Reflux;
methyl [3-chloro-5-(trifluoromethyl)-2-pyridinyl](cyano)acetate
658066-43-4

methyl [3-chloro-5-(trifluoromethyl)-2-pyridinyl](cyano)acetate

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

Conditions
ConditionsYield
With water; sodium chloride In dimethyl sulfoxide at 160℃;91%
With water; sodium chloride In dimethyl sulfoxide at 160℃;91%
With sodium chloride In water; dimethyl sulfoxide at 160℃;
ethyl 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-cyanoacetate

ethyl 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-cyanoacetate

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

Conditions
ConditionsYield
With hydrogenchloride In N,N-dimethyl-formamide at 130℃; for 4h; pH=2;86.2%
Stage #1: ethyl 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-cyanoacetate With hydrogenchloride In water; N,N-dimethyl-formamide for 6h; pH=3; Heating;
Stage #2: With potassium hydroxide In water at 20℃;
85%
With hydrogenchloride In water for 5h; Reflux;54 g
2,3-dichloro-5-trifluoromethylpyridine
69045-84-7

2,3-dichloro-5-trifluoromethylpyridine

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 2h; Solvent; Temperature; Reagent/catalyst;83%
(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyano-acetic acid tert-butyl ester

(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyano-acetic acid tert-butyl ester

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

Conditions
ConditionsYield
With trifluoroacetic acid
2,3-dichloro-5-trifluoromethylpyridine
69045-84-7

2,3-dichloro-5-trifluoromethylpyridine

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: t-BuOK / tetrahydrofuran
2: TFA
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / dimethyl sulfoxide / 0.25 h / 20 °C
1.2: 2.5 h / 80 °C
2.1: hydrogenchloride / N,N-dimethyl-formamide / 4 h / 130 °C / pH 2
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide / 1-methyl-pyrrolidin-2-one / 2.5 h / 70 - 80 °C
2: hydrogenchloride / water / 5 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / dimethyl sulfoxide / 12 h / 70 °C
2.1: hydrogenchloride / water; N,N-dimethyl-formamide / 6 h / pH 3 / Heating
2.2: 20 °C
View Scheme
ethyl acetate
141-78-6

ethyl acetate

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

2-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-3-oxo-butyronitrile
744209-92-5

2-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-3-oxo-butyronitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran100%
ethyl iodide
75-03-6

ethyl iodide

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]butanenitrile
856245-46-0

2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]butanenitrile

Conditions
ConditionsYield
Stage #1: 2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile With potassium tert-butylate In tetrahydrofuran at -5℃; for 2h;
Stage #2: ethyl iodide In tetrahydrofuran at 20℃;
100%
Stage #1: 2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile In tetrahydrofuran at -5℃; for 2h;
Stage #2: ethyl iodide at 20℃;
100%
2-trifluoromethylbenzoyl chloride
312-94-7

2-trifluoromethylbenzoyl chloride

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

fluopyram
658066-35-4

fluopyram

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; sodium carbonate In ethyl acetate at 60℃; under 15001.5 Torr; for 8h; Reagent/catalyst; Pressure; Solvent; Temperature;82%
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-1-ethanamine
658066-44-5

2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-1-ethanamine

Conditions
ConditionsYield
With hydrogen In tert-butyl methyl ether at 25℃; under 15001.5 Torr; for 4h; Autoclave;76.59%
With sulfuric acid; palladium on activated charcoal; tetrabutylammomium bromide; hydrogen In methanol at 20℃; under 3750.38 Torr; for 4h; Autoclave;70%
With hydrogen; 5%-palladium/activated carbon In acetic acid at 20℃; under 4500.45 Torr; for 15h; Product distribution / selectivity;19%
With sulfuric acid; 10 wt% Pd(OH)2 on carbon; hydrogen; sodium bromide In methanol at 20℃; under 3750.38 Torr; Reagent/catalyst;91.34 %Chromat.
With hydrogen; acetic anhydride at 80℃; for 4h; Reagent/catalyst; Temperature;
2-trifluoromethylbenzoyl chloride
312-94-7

2-trifluoromethylbenzoyl chloride

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-3-hydroxy-3-(2-(trifluoromethyl)phenyl)acrylonitrile

2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-3-hydroxy-3-(2-(trifluoromethyl)phenyl)acrylonitrile

Conditions
ConditionsYield
Stage #1: 2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h;
Stage #2: 2-trifluoromethylbenzoyl chloride In tetrahydrofuran; mineral oil for 1h;
75%
acetic anhydride
108-24-7

acetic anhydride

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

3-chloro-5-(trifluoromethyl)-2-ethylacetamide-pyridinyl

3-chloro-5-(trifluoromethyl)-2-ethylacetamide-pyridinyl

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In acetic acid at 20℃; under 22502.3 Torr; for 5h;71%
1-methyl-3-trifluoromethyl-1H pyrazole-4-carboxylic acid-anhydride
743456-60-2

1-methyl-3-trifluoromethyl-1H pyrazole-4-carboxylic acid-anhydride

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [2-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-ethyl]-amide
743456-54-4

1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [2-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-ethyl]-amide

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In acetonitrile at 0 - 20℃; for 4h;40%
methyl iodide
74-88-4

methyl iodide

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

A

2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]propanenitrile
1431842-75-9

2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]propanenitrile

B

2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropanenitrile
157763-90-1

2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-methylpropanenitrile

Conditions
ConditionsYield
Stage #1: 2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile With potassium tert-butylate In tetrahydrofuran at 5℃; for 2h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 5 - 20℃; for 72h; Inert atmosphere;
A 32%
B 22%
Stage #1: 2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile With potassium tert-butylate In tetrahydrofuran at 5℃; for 2h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 5 - 20℃; for 72h; Inert atmosphere;
A 32%
B 22%
Stage #1: 2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile With potassium tert-butylate In tetrahydrofuran at 5℃; for 2h;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 72h; Inert atmosphere;
A 32%
B 22%
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

4-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-5-methyl-2H-pyrazol-3-ylamine
744209-98-1

4-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-5-methyl-2H-pyrazol-3-ylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / sodium hydride / tetrahydrofuran
2: hydrazine hydrobromide / ethanol; H2O / Heating
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

7-chloro-3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine
744210-18-2

7-chloro-3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / sodium hydride / tetrahydrofuran
2: hydrazine hydrobromide / ethanol; H2O / Heating
3: dioxane / Heating
4: POCl3 / acetonitrile / Heating
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-ol
744210-07-9

3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / sodium hydride / tetrahydrofuran
2: hydrazine hydrobromide / ethanol; H2O / Heating
3: dioxane / Heating
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-dipropyl-amine

[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-dipropyl-amine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / sodium hydride / tetrahydrofuran
2: hydrazine hydrobromide / ethanol; H2O / Heating
3: dioxane / Heating
4: POCl3 / acetonitrile / Heating
5: acetonitrile / Heating
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-bis-(2-methoxy-ethyl)-amine

[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-bis-(2-methoxy-ethyl)-amine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / sodium hydride / tetrahydrofuran
2: hydrazine hydrobromide / ethanol; H2O / Heating
3: dioxane / Heating
4: POCl3 / acetonitrile / Heating
5: acetonitrile / Heating
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

butyl-[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-propyl-amine

butyl-[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-propyl-amine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / sodium hydride / tetrahydrofuran
2: hydrazine hydrobromide / ethanol; H2O / Heating
3: dioxane / Heating
4: POCl3 / acetonitrile / Heating
5: acetonitrile / Heating
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-cyclopropylmethyl-propyl-amine

[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-cyclopropylmethyl-propyl-amine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / sodium hydride / tetrahydrofuran
2: hydrazine hydrobromide / ethanol; H2O / Heating
3: dioxane / Heating
4: POCl3 / acetonitrile / Heating
5: acetonitrile / Heating
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

benzyl-[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-propyl-amine

benzyl-[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-propyl-amine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / sodium hydride / tetrahydrofuran
2: hydrazine hydrobromide / ethanol; H2O / Heating
3: dioxane / Heating
4: POCl3 / acetonitrile / Heating
5: acetonitrile / Heating
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

dibutyl-[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-amine

dibutyl-[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl]-amine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / sodium hydride / tetrahydrofuran
2: hydrazine hydrobromide / ethanol; H2O / Heating
3: dioxane / Heating
4: POCl3 / acetonitrile / Heating
5: acetonitrile / Heating
View Scheme
acetic acid
64-19-7

acetic acid

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethanamine acetate
658066-45-6

[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethanamine acetate

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon at 20℃; under 3750.38 Torr;
1-Bromo-2-chloroethane
107-04-0

1-Bromo-2-chloroethane

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropanecarbonitrile
1433906-75-2

1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropanecarbonitrile

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 60℃; for 3h;
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

2-methyl-propane-2-sulfinic acid 1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-methylidene amide
1433906-77-4

2-methyl-propane-2-sulfinic acid 1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-methylidene amide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water / 3 h / 60 °C
2: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 144 h / -78 - 20 °C
3: titanium(IV) tetraethanolate / tetrahydrofuran / 24 h / 20 °C
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-ethylamine
1433906-72-9

1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-ethylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water / 3 h / 60 °C
2.1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 144 h / -78 - 20 °C
3.1: titanium(IV) tetraethanolate / tetrahydrofuran / 24 h / 20 °C
4.1: dichloromethane; diethyl ether / 18 h / -48 - 20 °C
4.2: 2 h / 20 °C
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

N-{1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-ethyl}-2,6-difluoro-benzamide
1433905-35-1

N-{1-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-ethyl}-2,6-difluoro-benzamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water / 3 h / 60 °C
2.1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 144 h / -78 - 20 °C
3.1: titanium(IV) tetraethanolate / tetrahydrofuran / 24 h / 20 °C
4.1: dichloromethane; diethyl ether / 18 h / -48 - 20 °C
4.2: 2 h / 20 °C
5.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
View Scheme
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
157764-10-8

2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile

C-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-methylamine
1433906-73-0

C-[1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-methylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water / 3 h / 60 °C
2: ammonia; hydrogen / methanol / 17 h / 20 °C / 2250.23 Torr / Sealed tube
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide; benzyltri(n-butyl)ammonium chloride / acetonitrile / 20 °C / Inert atmosphere
2: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 0 - 20 °C / Inert atmosphere
3: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
View Scheme

157764-10-8Relevant articles and documents

Design, synthesis biological activity, and docking of novel fluopyram derivatives containing guanidine group

Liang, Peibo,Shen, Shengqiang,Xu, Qingbo,Wang, Simin,Jin, Shuhui,Lu, Huizhe,Dong, Yanhong,Zhang, Jianjun

, (2021)

Succinate dehydrogenase (SDH), a crucial bridge enzyme between the respiratory electron transfer chain and tricarboxylic acid (or Krebs) cycle, has been identified as an ideal target for the development of effective fungicide. In this study, a series of 24 novel SDH inhibitors (SDHIs) were designed, synthesized, and characterized by 1H NMR, 13C NMR, and HRMS. In vitro fungicidal activity experiments, most of the compounds exhibited broad-spectrum antifungal activities against five plant pathogenic fungi. Compounds 9j and 9k showed excellent activities against Pythium aphanidermatum with EC50 values of 9.93 mg/L and 10.50 mg/L, respectively, which were superior to the lead compound Fluopyram with an EC50 value of 19.10 mg/L. Furthermore, the toxicity of these compounds was also tested against Meloidogyne incognita J2 nematodes. The results indicated that compound 9x exhibited moderate nematicidal activity (LC50/48 h = 71.02 mg/L). Molecular docking showed that novel guanidine amide of 9j formed hydrogen bonds with crucial residues, which was crucial to the binding of an inhibitor and SDH. This present work indicates that these derivatives may serve as novel potential fungicides targeting SDH.

Synthesis method of benzamide compound (by machine translation)

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Paragraph 0048-0050; 0056; 0057; 0060; 0061; 0064; 0065, (2020/05/05)

The synthesis method of N - [2 - [3 -(trifluoromethyl)-pyridin - 2 2-yl] ethyl] - 2 - (Trifluoromethyl-)-ethyl- Trifluoromethyl-2,3 -trifluoromethyl) benzamide,) yields, chloro - 5 5 5-(trifluoromethyl pH=2-5 pyri- 2 2-based N,N -Trifluoromethyl-3 -Trifluoromethyl) - 2 -ethyl,trifluoromethyl-3 -benzamide,).) - 2 - The synthesis method employed in the present invention is obtained by catalytic hydrogenation . The N - [2 - [3 - reaction mother liquid 2 - (obtained by the present invention is synthesized by a method of, synthesizing)% N - [2 - [3 -chloro - 5 5 5-(trifluoromethylpyridin - 2 2-methyl-).trifluoromethylpyridine]) as a starting material under the action, of a, catalyst and a base by, catalytic hydrogenation to obtain a compound] - 2 - (g - 5) 5 5-] (] - 2 - (trifluormethyl) pyridine)-2-). trifluoromethylbenzenesulfonamide. (by machine translation)

Fluopyram preparation method

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Paragraph 0036-0054, (2019/02/13)

The invention relates to a fluopyram preparation method, which sequentially comprises: (1) carrying out a substitution reaction on 2,3-dichloro-5-trifluoromethylpyridine and ethyl cyanoacetate or methyl cyanoacetate at a temperature of 30-160 DEG C in the presence of an alkali and a solvent, adjusting the reaction liquid to an acidic pH value after completing the reaction, and carrying out a decarboxylation reaction at a temperature of 80-160 DEG C to obtain 3-chloro-5-(trifluoromethyl)-2-acetonitrilepyridine; and (2) carrying out tandem hydrogenation and condensation reaction on the 3-chloro-5-(trifluoromethyl)-2-acetonitrilepyridine prepared in the step (1) and o-trifluoromethylbenzoyl chloride at a temperature of 20-100 DEG C in the presence of a catalyst, hydrogen, an alkali and a solvent to obtain fluopyram. According to the present invention, the preparation method has the short steps, avoids the unnecessary protection-deprotection step, is economical and environmentally friendly, and is suitable for industrial production.

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