5-bromo-2-(methylthio)nicotinic acid

Base Information

• Chemical Name: 5-bromo-2-(methylthio)nicotinic acid
• CAS No.: 1220422-10-5
• Molecular Formula: C₇H₆BrNO₂S
• Molecular Weight: 248.1
• Mol file: 1220422-10-5.mol

Synonyms:

Chemical Property of 5-bromo-2-(methylthio)nicotinic acid

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

5-Bromo-2-(methylthio)nicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-bromo-2-(methylthio)nicotinic acid

There total 2 articles about 5-bromo-2-(methylthio)nicotinic acid 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: 92.0%

5-bromo-2-fluoro-pyridine-3-carboxylic acid (29241-66-5) + sodium thiomethoxide (5188-07-8) → 5-bromo-2-(methylthio)nicotinic acid (1220422-10-5)

Guidance literature:

5-bromo-2-fluoro-pyridine-3-carboxylic acid; With potassium carbonate; In N,N-dimethyl-formamide; at 0 ℃; for 0.116667h;

sodium thiomethoxide; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere; Sealed tube;

Reference yield: 92.0%

sodium thiomethanolate + 5-bromo-2-fluoro-pyridine-3-carboxylic acid (29241-66-5) → 5-bromo-2-(methylthio)nicotinic acid (1220422-10-5)

Guidance literature:

5-bromo-2-fluoro-pyridine-3-carboxylic acid; With potassium carbonate; In N,N-dimethyl-formamide; at 0 ℃; for 0.116667h; Inert atmosphere;

sodium thiomethanolate; Sealed tube; Inert atmosphere;

Reference yield:

5-bromo-2-(methylthio)nicotinic acid (1220422-10-5) → 3-fluoro-5-((1-(methylsulfonyl)-5,6-dihydrospiro[cyclopenta[c]pyridine-7,2'-[1,3]dioxolan]-4-yl)oxy)benzonitrile

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -50 °C

1.2: 0.25 h

2.1: lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 25 °C

2.2: 2 h

3.1: cobalt(II) chloride hexahydrate; sodium tetrahydroborate; methanol / 0 °C / Inert atmosphere; Sealed tube

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C

4.2: 0.67 h / 150 °C / Microwave irradiation; Sealed tube

5.1: Oxone / water; methanol / 24 h / 0 °C

6.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 - 20 °C

6.2: 0.17 h

7.1: t-BuBrettPhos; potassium hydroxide; [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate / water; 1,4-dioxane / 1.5 h / 80 °C / Inert atmosphere; Sealed tube

8.1: potassium carbonate / acetonitrile / 0.17 h / 25 °C

8.2: 3 h / 50 °C

With 2,2,6,6-tetramethyl-piperidine; methanol; Oxone; sodium tetrahydroborate; n-butyllithium; cobalt(II) chloride hexahydrate; trimethylsilyl trifluoromethanesulfonate; t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetonitrile;

upstream raw materials:

5-bromo-2-fluoro-pyridine-3-carboxylic acid

sodium thiomethoxide

Refernces

• 1、 -. "COMPOSITIONS FOR USE IN TREATING PULMONARY ARTERIAL HYPERTENSION". Paragraph 00552. . Retrieved 2016/09/26.
• 2、 -. "SUBSTITUTED PYRIDINES AND USES THEREOF". Paragraph 0445. . Retrieved 2016/09/26.