Isobutyryl chloride → HCID 21431531, compound

HRID 731723Notes

Reaction equation

HRID 731723 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.[C:13](Cl)(=[O:17])[CH:14]([CH3:16])[CH3:15].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[CH3:1][N:2]([CH3:12])[C:3]1[C:11]([C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 20322001HCID 20322001, compound

Product 1

HCID 21431531HCID 21431531, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 560 mg (3.45 mmol) of N,N-dimethylpyrazolo[1,5-a]pyridin-2-amine, 355 μl (3.45 mmol) of isobutyryl chloride and 100 mg of AlCl3 was stirred in 3 ml of DCE at RT overnight. The mixture was quenched with saturated NH4Cl and extracted with EtOAc, and the crude product was purified on an Al2O3 column to provide 208 mg of 1-(2-(dimethylamino)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one. Compound 1072.

Workup

  1. customThe mixture was quenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. customthe crude product was purified on an Al2O3 column

Sources & evidence

ORD record
ord-d49e6ed5b2224b2f887aa367f63d7579
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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