Trimethylsilyl cyanide → Furo[3,2-c]pyrazolo[1,5-a]pyridin-1-ylacetonitrile

HRID 2389880Notes

Reaction equation

HRID 2389880 reaction equation
C[Si]([C:5]#[N:6])(C)C.[C:7]1([CH2:19]O)[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]3[O:16][CH:17]=[CH:18][C:12]=3[C:11]=12>ClCCl.C(=O)([O-])O.[Na+]>[C:7]1([CH2:19][C:5]#[N:6])[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]3[O:16][CH:17]=[CH:18][C:12]=3[C:11]=12

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 59179399Furo[3,2-c]pyrazolo[1,5-a]pyridin-1-ylmethanol

Product 1

HCID 59179369Furo[3,2-c]pyrazolo[1,5-a]pyridin-1-ylacetonitrileYield 55%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of boron trifluoride diethyl ether complex (200 μL, 1.58 mmol) and trimethylsilyl cyanide (280 μL, 2.10 mmol) in dichloromethane (5 mL) was added a solution of furo[3,2-c]pyrazolo[1,5-a]pyridin-1-ylmethanol (100 mg, 0.531 mmol) in dichloromethane (5 mL) under ice-cooling and an argon atmosphere, and the mixture was stirred for 30 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70) to give the title compound (57.1 mg, yield 55%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70)

Sources & evidence

ORD record
ord-a9241e2272ac488380aeeb3a8f931cf5
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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