Methyl 2-chloroacrylate → dimethyl 13-cyclohexyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl chloroacrylate (1.7 eq), triethylbutyl ammonium chloride (0.2 eq) and potassium carbonate (6 eq) were added to a solution of methyl 2-(2-aminophenyl)-3-cyclohexyl-1H-indole-6-carboxylate in dry MeCN (0.02 M). The mixture was heated at 60° C. overnight. The mixture was allowed to cool to RT, filtered and concentrated in vacuo. The residue was taken up in MeOH and 5 eq of trimethylsilyldiazomethane (2 N solution in hexanes) added dropwise. Volatiles were then removed in vacuo and the crude product was purified by flash chromatography (SiO2; 2:8 EtOAc/PE) to afford the title compound as a solid (45%). MS (ES+) m/z 433 (M+H)+.

Provenance & Evidence