Potassium Cyanide → 1H-Indazole-5-carbonitrile

HRID 1931349Notes

Reaction equation

HRID 1931349 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si](C(C)(C)C)(C)C)[C:5]2=[N:6][CH:7]=1.[C-:18]#[N:19].[K+]>[Cu].[Pd].CN(C=O)C>[C:5]([C:4]1[CH:3]=[C:2]2[C:7](=[CH:9][CH:10]=1)[NH:6][N:19]=[CH:18]2)#[N:8]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 497590181H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(1,1-dimethylethyl)dimethylsilyl]-

Product 1

HCID 111263841H-Indazole-5-carbonitrile

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

Compound 19 can be cyanated with, for example, KCN in heating DMF in the presence of a catalyst such as, copper or palladium to provide the 5-cyano azaindole 46.

Sources & evidence

ORD record
ord-3940887e2de840b4ab3e3c3d7f53d365
Source dataset
uspto-grants-2012_05
Patent number
US08188281B2

Reaction notes

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