2-Propanethiol → 6-Isopropylsulfanyl-pyridine-2-carboxylic acid methyl ester

HRID 62858

Reaction equation

HRID 62858 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Br)[N:6]=1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:18][CH:19]([SH:21])[CH3:20]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:21][CH:19]([CH3:20])[CH3:18])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 10796Cesium carbonateHCID 16217886Methyl 6-bromopyridine-2-carboxylate

Product 1

HCID 901182976-Isopropylsulfanyl-pyridine-2-carboxylic acid methyl esterYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-pyridine-2-carboxylic acid methyl ester (0.15 g, 0.69 mmol) was added with DMF (2.3 mL), Cs2CO3(0.45 g, 1.38 mmol) and 2-propanethiol (0.064 mL, 0.69 mmol) in turn, and the mixture was stirred at room temperature for 18 hours. After the termination of the reaction, the reactant was filtered and concentrated under reduced pressure to obtain the title compound (0.13 g, 88%).

Workup

  1. customAfter the termination of the reaction
  2. filtrationthe reactant was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-792a4140021c4e56b730b7d41a6c301c
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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