Water → S-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-1-oxopropan-2-yl ethanethioate

HRID 731733Notes

Reaction equation

HRID 731733 reaction equation
Cl[CH:2]([CH3:17])[C:3]([C:5]1[C:6]([CH:14]([CH3:16])[CH3:15])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12)=[O:4].[C:18]([O-:21])(=[S:20])[CH3:19].[K+].CCOC(C)=O.O>CN(C=O)C>[C:18](=[O:21])([S:20][CH:2]([CH3:17])[C:3]([C:5]1[C:6]([CH:14]([CH3:16])[CH3:15])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12)=[O:4])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 215857512-Chloro-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanoneHCID 23670855Potassium ethanethioate

Product 1

HCID 57837471S-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-1-oxopropan-2-yl ethanethioateYield 55.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one (0.9 g, 1 equivalent) and potassium thioacetate (0.61 g, 1.5 equivalents) in 4 mL of DMF was stirred at room temperature for 1 hour. The resulting solution was worked up with EtOAc and water. The crude product was purified by silica gel flash column chromatography to give S-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-1-oxopropan-2-yl ethanethioate (0.58 g, 55% yield) as a yellow solid. Compound 1081.

Workup

  1. customThe crude product was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-06374986e0274607a5651ac49d89401b
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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