methyl 4-allyl-6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate → Methyl 12-cyclohexyl-7H-thieno[2',3':4,5]pyrrolo[2,1-a][2]benzazepine-10-carboxylate

Participants

Reaction Steps

Methyl 4-allyl-6-cyclohexyl-5-(2-vinylphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate was dissolved in DCM (0.02M) and treated with Zhan catalyst (dichloro(5-chloro-2-isopropoxybenzylidene)(1,3-dimesityl-1,3-dihydro-2H-imidazol-2-ylidene)ruthenium; RC-301; 0.3 eq.) at 35° C. for 2 h. After removal of the solvent the residue was purified by chromatography (PE/EtOAc 14:1) to afford the title compound in 83% yield. 1H-NMR (400 MHz, CDCl3, 300 K, δ) 7.74 (s, 1H), 7.57-7.56 (m, 1H), 7.45-7.35 (m, 3H), 6.82 (d, 1H, J 10.4), 6.30-6.25 (m, 1H), 4.47 (bs, 2Hs), 3.93 (s, 3H), 2.83-2.76 (m, 1H), 1.85-1.29 (m, 10H); MS (ES+) m/z 378 (M+H)+.

Provenance & Evidence