Propionyl chloride → HCID 10910951, compound

HRID 731724Notes

Reaction equation

HRID 731724 reaction equation
[CH:1]([C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[C:13](Cl)(=[O:16])[CH2:14][CH3:15].[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[CH:1]([C:4]1[C:12]([C:13](=[O:16])[CH2:14][CH3:15])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Product 1

HCID 10910951HCID 10910951, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A mixture of 6.4 g (40 mmol) of 2-isopropylpyrazolo[1,5-a]pyridine, 3.7 g (40 mmol) of propionyl chloride and 400 mg of AlCl3 was stirred at RT in 5 ml of CS2 for 3 days. The mixture was quenched with saturated NH4Cl and extracted with EtOAc to provide 5.44 g of crude 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one, which was purified on a silica gel column to yield 700 mg of pure intermediate along with 3.53 g of starting material. 700 mg of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one was reacted with 600 μl of 1M t-BuOK in t-BuOH at −20° C. for 20 minutes, followed by the addition of 600 μl of isoamylnitrite at 0° C. and stirring at RT overnight. The mixture was quenched with saturated NH4Cl and extracted with EtOAc to provide 1.2 g of crude product, which was purified on a silica gel column to furnish 314 mg of (Z)-2-(hydroxyimino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one. Compound 1083.

Workup

  1. customThe mixture was quenched with saturated NH4Cl
  2. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-1c7151c5ae7e4ceb8139cd31024c758f
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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