Dimethylformamide → HCID 71020563, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the benzonitrile of Preparation 15 (800 mg, 3.5 mmol) in N,N-dimethylformamide (10 ml), under nitrogen, were added potassium carbonate (580 mg, 4.2 mmol) and di-tert-butyl dicarbonate (915 mg, 4.2 mmol), dissolved in N,N-dimethylformamide (10 ml). The reaction mixture was stirred at 50° C. for 6 hours. It was then partitioned between ethyl acetate (100 ml) and water (200 ml). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×50 ml). The organic extracts were combined, dried over magnesium sulphate, filtered and evaporated to give a pale orange solid, which was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (99:1, by volume). Trituration of the solid with diisopropyl ether:pentane provided the title compound as a cream coloured solid (842 mg, 73%).

Provenance & Evidence