Acetyl chloride → 1-[2-(Propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]ethan-1-one

HRID 731735Notes

Reaction equation

HRID 731735 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH:9]([C:12]1[CH:20]=[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1)([CH3:11])[CH3:10].C([O-])(O)=O.[Na+]>ClCCl.CCOC(C)=O>[CH:9]([C:12]1[C:20]([C:5](=[O:7])[CH3:6])=[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1)([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Product 1

HCID 159338551-[2-(Propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]ethan-1-oneYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid aluminum chloride (0.82 g, 2 equivalents) was added to a solution of acetyl chloride (0.24 mL, 1.1 equivalents) in 1 mL of dichloromethane and the solution was stirred at room temperature for 40 minutes. Neat 2-isopropylpyrazolo[1,5-a]pyridine (0.5 g, 1 equivalent) was added dropwise to this solution at room temperature (exotherm was observed), and the resulting solution was stirred at room temperature for 20 hours and worked up with EtOAc and saturated NaHCO3. The crude product was purified by silica gel flash column chromatography to give 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)ethanone (0.29 g, 46% yield) as a solid. Compound 1080.

Workup

  1. stirringthe resulting solution was stirred at room temperature for 20 hours
  2. customThe crude product was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-c9c43f1d4ff747c68bc55a28800a3668
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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