Dimethylformamide → HCID 178426390, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-bromo-7-methyl-1H-benzimidazole obtained in step 1 (2.80 g; 13.27 mmol), zinc cyanide (934 mg; 7.96 mmol), tris(dibenzylideneacetone)dipalladium (364 mg; 0.40 mmol), 1,1′-bis(diphenylphosphino)ferrocene (551 mg; 0.99 mmol), zinc (34 mg; 0.53 mmol) and zinc acetate (97 mg; 0.53 mmol) in dry DMF (28 mL) under inert atmosphere was heated at 120° C. for 16 hours. Reaction mixture was filtered over a pad of celite and washed with EtOAc. The organics were washed with water, dried over MgSO4 and evaporated under vacuum to afford a brown solid that was triturated with EtOH, filtered to give the title compound as a beige solid. 1H NMR (DMSO-d6) δ 13.11 (br s, 1H), 8.45 (s, 1H), 8.02-7.90 (m, 1H), 7.42 (m, 1H), 2.54 (m, 3H). LC/MS (Method B): 158.2 (M+H)+.

Provenance & Evidence