Trimethylsilyl cyanide → 1H-Pyrazolo[4,3-b]pyridine-5-carbonitrile

HRID 218466Notes

Reaction equation

HRID 218466 reaction equation
O[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[NH+:8](COCC[Si](C)(C)C)[NH:9][CH:10]=[C:3]12.[Si]([C:23]#[N:24])(C)(C)C>C(Cl)Cl>[NH:8]1[C:4]2[C:3](=[N:2][C:7]([C:23]#[N:24])=[CH:6][CH:5]=2)[CH:10]=[N:9]1

Participants

4

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 131729774HCID 131729774, compound

Product 1

HCID 602096591H-Pyrazolo[4,3-b]pyridine-5-carbonitrileYield 115.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-hydroxy-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazolo[4,3-b]pyridinium (1.59 g, 6 mmol) in DCM (130 mL) was added TMSCN (1.13 mL, 9 mmol). After 5 min at rt, (Me)2N(C(O)Cl (0.83 mL, 9 mmol) was added. The reaction mixture was stirred at rt for 4 days, after which it was diluted with DCM, washed with brine, and dried. Concentration followed by purification through column afforded 1H-pyrazolo[4,3-b]pyridine-5-carbonitrile (1 g, 61%).

Workup

  1. addition(Me)2N(C(O)Cl (0.83 mL, 9 mmol) was added
  2. washwashed with brine
  3. customdried
  4. concentrationConcentration
  5. customfollowed by purification through column

Sources & evidence

ORD record
ord-c6129fa044b340f3837bb8fedc46154b
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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