Dimethylformamide → 4-methyl-1H-benzimidazole-5-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	5-Bromo-4-methyl-1H-benzo[d]imidazole	HCID 59214444	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Zinc	HCID 23994	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	4-methyl-1H-benzimidazole-5-carbonitrile	HCID 45120550	53%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 158 (21 g; 99 mmol), Zn(CN)2 (23.2 g; 198 mmol), Pd(dppf)Cl2 (6.4 g; 9.9 mmol) and zinc (258 mg; 4 mmol) in dry DMF (150 mL) under inert atmosphere was heated at 120° C. for 2 h. The reaction mixture was filtered through a pad of Celite® that was washed with EtOAc. The organics were washed with water, dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by SiO2 chromatography eluted with a DCM/MeOH gradient (0 to 10% MeOH) to afford 8.3 g (53%) of 4-methyl-1H-benzo[d]imidazole-5-carbonitrile (160) as a brown solid: MS (ESI) m/z=158 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08637537B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-b33e15483cc141048504e9b864486d02
Source note	uspto-grants-2014_01