Methyl 3-cyclohexyl-1-(2-(methoxycarbonyl)allyl)-2-(2-vinylphenyl)-1H-indole-6-carboxylate → Methyl 13-cyclohexyl-6-(carbomethoxy)-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-cyclohexyl-1-(2-(methoxycarbonyl)allyl)-2-(2-vinylphenyl)-1H-indole-6-carboxylate (13, R=methyl), (3.1 g, 6.77 mmol) and Grubbs' 2nd generation catalyst (1.7 g, 1.35 mmol) in methylene chloride (350 mL) were heated at 45° C. for 96 hr. Solvent was removed in vacuo and the residue was chromatographed on silica gel using hexane/ethyl acetate (0-15%) to afford pure title compound as a bright yellow solid (1.36 g). The mixed fractions were combined and concentrated in vacuo and the residue was recrystallized using methanol to afford the title compound (175 mg). Total title compound obtained: 1.805 g, 53%. ESI-MS m/z 430 (MH+).

Provenance & Evidence