Trimethylsilyl cyanide → (2-Ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)acetonitrile

HRID 2389931Notes

Reaction equation

HRID 2389931 reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH2:7]([C:9]1[C:21]([CH2:22]O)=[C:12]2[C:13]3[CH:19]=[C:18]([CH3:20])[O:17][C:14]=3[CH:15]=[CH:16][N:11]2[N:10]=1)[CH3:8].C(=O)([O-])O.[Na+]>ClC1C=CC=CC=1>[CH2:7]([C:9]1[C:21]([CH2:22][C:5]#[N:6])=[C:12]2[C:13]3[CH:19]=[C:18]([CH3:20])[O:17][C:14]=3[CH:15]=[CH:16][N:11]2[N:10]=1)[CH3:8]

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 591794472-Ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridine-1-methanol

Product 1

HCID 59179451(2-Ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)acetonitrileYield 71.2%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

Under an argon atmosphere, to a solution of boron trifluoride diethyl ether complex (0.563 mL, 4.44 mmol) and trimethylsilyl cyanide (0.789 mL, 5.92 mmol) in chlorobenzene (30 mL) was added a solution of (2-ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)methanol (340 mg, 1.48 mmol) in chlorobenzene (15 mL) under ice-cooling, and the mixture was stirred at room temperature for 15 min. A saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. 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 (252 mg, yield 71%).

Workup

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

Sources & evidence

ORD record
ord-12d63686161b43848ab82afc3a4e5c51
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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