Dimethylformamide → HCID 178510114, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-bromo-7-fluoro-1H-benzimidazole obtained from step 1 (2.50 g; 11.63 mmol), zinc cyanide (Adrich, 819 mg; 6.98 mmol), tris(dibenzylideneacetone)dipalladium (Adrich, 319 mg; 0.35 mmol), 1,1-bis(diphenylphosphino)ferrocene (483 mg; 0.87 mmol), zinc (Adrich, 30 mg; 0.47 mmol) and zinc acetate (Adrich, 85 mg; 0.47 mmol) in dry DMF (25 mL) under inert atmosphere was heated at 120° C. for 16 hours. Reaction mixture was filtered over a pad of celite 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 and filtered to give the title compound as a brown solid 1H NMR (DMSO-d6) δ 13.40 (bs, 1H), 8.55 (s, 1H), 8.04 (s, 1H), 7.51-7.48 (d, J=10.7 Hz, 1H). LC/MS (Method B): 162.1 (M+H)+.

Provenance & Evidence