Dimethylformamide → 6-Sec-butylsulfanyl-pyridine-2-carboxylic acid ethyl ester

HRID 62839Notes

Reaction equation

HRID 62839 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([SH:12])[N:7]=1)=[O:5])[CH3:2].CN(C=O)C.[H-].[Na+].I[CH:21]([CH2:23][CH3:24])[CH3:22]>O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12][CH:21]([CH2:23][CH3:24])[CH3:22])[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 105592-IodobutaneHCID 24758Sodium hydrideHCID 178468955HCID 178468955, compound

Product 1

HCID 901182566-Sec-butylsulfanyl-pyridine-2-carboxylic acid ethyl esterYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

6-Mercapto-pyridine-2-carboxylic acid ethyl ester (0.25 g, 1.3 mmol) was added with DMF (7 mL), and the mixture was cooled to 0° C. NaH (0.065 g, 1.56 mmol) was added thereto, and the mixture was stirred for 30 minutes. 2-Iodobutane (0.2 mL, 1.56 mmol) was added thereto, and the mixture was stirred at room temperature for 3 hours. The reactant was added with water and then extracted with EtOAc. The organic layer was separated, dried with MgSO4, and purified by column chromatography to obtain the title compound (0.17 g, 52%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-47cb329d23174e0c9f10f42c35dd4706
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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