Trimethylsilyl cyanide → 2-(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)propanenitrile

HRID 2389926Notes

Reaction equation

HRID 2389926 reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH2:7]([C:9]1[C:20]([CH:21](O)[CH3:22])=[C:12]2[C:13]3[CH2:19][CH2:18][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:20]([CH:21]([CH3:22])[C:5]#[N:6])=[C:12]2[C:13]3[CH2:19][CH2:18][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 591794601-(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethanol

Product 1

HCID 591793972-(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)propanenitrileYield 75%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

Under an argon atmosphere, to a solution of boron trifluoride diethyl ether complex (0.411 mL, 3.24 mmol) and trimethylsilyl cyanide (0.576 mL, 4.32 mmol) in chlorobenzene (10 mL) was added a solution of 1-(2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethanol (250 mg, 1.08 mmol) in chlorobenzene (20 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=5/95→40/60) to give the title compound (195 mg, yield 75%).

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=5/95→40/60)

Sources & evidence

ORD record
ord-f91681a56f3c47c98ced2a0262df1337
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

Loading…