2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide

Base Information

• Chemical Name: 2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide
• CAS No.: 1258298-20-2
• Molecular Formula: C₁₇H₁₃Cl₂N₃O₃
• Molecular Weight: 378.215
• Mol file: 1258298-20-2.mol

Synonyms:2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide

Chemical Property of 2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide

There total 11 articles about 2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-vinylbenzamide (1258298-19-9) → 2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide (1258298-20-2)

Guidance literature:

With ozone; In methanol; dichloromethane; at -78 ℃; for 0.116667h;

Reference yield:

trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-2,6-dichloro-phenyl ester (1098619-84-1) → 2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide (1258298-20-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: palladium diacetate; triethylamine; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 7600.51 Torr

2.1: sulfuric acid / ethyl acetate / 2 h / 20 °C

3.1: hydrogenchloride; sodium nitrite / water / 0.5 h / -5 - 0 °C

3.2: 20 °C

4.1: pyridine; lithium iodide / water / 30 h / 130 °C

5.1: thionyl chloride / Reflux; Inert atmosphere

6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

6.2: 12 h / 0 - 25 °C / Inert atmosphere

7.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere

8.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 2 h / 140 °C / Sealed tube; Inert atmosphere; Microwave irradiation

9.1: ozone / dichloromethane; methanol / -78 °C

9.2: -78 °C / Inert atmosphere

With pyridine; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; sulfuric acid; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; sodium hydride; sodium carbonate; caesium carbonate; ozone; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium iodide; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm400266t

Reference yield:

methyl 4-amino-2,6-dichlorobenzoate (232275-49-9) → 2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide (1258298-20-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / -5 - 0 °C

1.2: 20 °C

2.1: pyridine; lithium iodide / water / 30 h / 130 °C

3.1: thionyl chloride / Reflux; Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

4.2: 12 h / 0 - 25 °C / Inert atmosphere

5.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere

6.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 2 h / 140 °C / Sealed tube; Inert atmosphere; Microwave irradiation

7.1: ozone / dichloromethane; methanol / -78 °C

7.2: -78 °C / Inert atmosphere

With pyridine; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; sodium hydride; sodium carbonate; caesium carbonate; ozone; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium iodide; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm400266t

upstream raw materials:

2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-vinylbenzamide

trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-2,6-dichloro-phenyl ester

methyl 4-amino-2,6-dichlorobenzoate

2,6-dichloro-4-iodo-benzoic acid methyl ester

Downstream raw materials:

2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-((dimethylamino)methyl)benzamide

(±)-2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-(1-hydroxyethyl)benzamide

2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-((methylamino)methyl)benzamide

2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-(2-hydroxypropan-2-yl)benzamide

Refernces

• 1、 -. "JANUS KINASE INHIBITOR COMPOUNDS AND METHODS". Page/Page column 109. . Retrieved 2010/12/29.