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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2409027Generated: October 31, 2026

Dimethylformamide → 3H-Imidazo[4,5-c]pyridine-7-carbonitrile

https://huagongshe.com/reaction/2409027

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantAmmonium HydroxideHCID 14923—
ReactantHCID 178419455HCID 178419455—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystHCID 178418397HCID 178418397—
Product3H-Imidazo[4,5-c]pyridine-7-carbonitrileHCID 7055717267%

Reaction Steps

To a solution of 7-bromo-1H-imidazo[4,5-c]pyridine (3 g, 15.6 mmol) in DMF (10 mL) was added Pd(PPh3)4 (1.0 g) and Zn(CN)2 (1.2 g, 10 mmol). The reaction mixture was irradiated in a microwave at 100° C. for 2 h under Ar. The reaction mixture was poured into aqueous NH4OH and extracted with DCM. The organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography to afford 1.5 g (67%) of 3H-imidazo[4,5-c]pyridine-7-carbonitrile as a white solid; MS (ESI)/v/z: 145.0 [M+1]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08815877B2
Source datasetuspto-grants-2014_08
ORD IDord-e0b482a1005b465b88aeba75d68f5a5e
Source noteuspto-grants-2014_08