Isobutyryl chloride → 1-(2-Methoxypyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one

HRID 731721Notes

Reaction equation

HRID 731721 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.[C:12](Cl)(=[O:16])[CH:13]([CH3:15])[CH3:14].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[CH3:1][O:2][C:3]1[C:11]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[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 122844272-Methoxypyrazolo[1,5-a]pyridine

Product 1

HCID 578375231-(2-Methoxypyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-oneYield 31.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 700 mg (4.7 mmol) of 2-methoxypyrazolo[1,5-a]pyridine, 550 mg of isobutyryl chloride and 300 mg of AlCl3 was stirred in 2 ml of DCE at RT for 5 hours. The reaction was quenched with saturated NH4Cl and extracted with ethyl acetate to yield 1 g of crude product. Purification on an Al2O3 column furnished 323 mg of 1-(2-methoxypyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one. Compound 1055.

Workup

  1. customThe reaction was quenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. customto yield 1 g of crude product
  4. customPurification on an Al2O3 column

Sources & evidence

ORD record
ord-3d8528f042ba4eb88cf8545a86b21577
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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