5-allyl-4-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole → 5-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene

Participants

Reaction Conditions

Reaction Steps

5-Allyl-4-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.25 mmol) was dissolved in DCM (15 mL) and purged with nitrogen. Hoveyda-Grubbs 2nd generation catalyst (10 mg, 0.015 mmol) was added and the reaction mixture was re-purged with nitrogen. The reaction mixture was heated at 80° C. for 6 h, cooled to RT, concentrated under reduced pressure and the residue purified by column chromatography using silica (100-200 mesh) eluting with 1% MeOH in DCM to obtain 87 mg of 5-(4-fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene. 1H NMR (Oxalate salt, CD3OD) δ (ppm): 7.40 (m, 2H), 7.30 (d, 1H), 7.26 (s, 1H), 7.05 (m, 3H), 6.06 (d, 1H), 5.22 (m, 1H), 4.76 (m, 1H), 4.60-4.40 (m, 2H), 3.60 (m, 2H), 3.18 (s, 3H), 3.05 (m, 1H), 2.70 (m, 1H), 2.40 (s, 3H), 1.66 (s, 3H).

Provenance & Evidence