4-allyl-5-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole → 6-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene

Participants

Reaction Steps

To a solution of the 4-allyl-5-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (250 mg, 0.64 mmol) in degassed DCM (7 mL) was added dropwise a solution of Grubbs'2nd generation catalyst (27.61 mg, 0.0325 mmol, 5 mol %) in degassed DCM (3 mL) under an nitrogen atmosphere. The resultant solution was heated at 115° C. for 1 h in a microwave. The solvent was evaporated in vacuo and the residue was purified by reverse HPLC to obtain 6-(4-fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene as an off white solid (50 mg). 1H NMR (Freebase, CDCl3) δ (ppm): 7.40 (m, 2H), 7.30 (d, 1H), 7.10 (d, 1H), 7.04-6.98 (m, 2H), 5.99 (d, 1H), 4.96 (d, 1H), 3.99 (d, 1H), 3.96 (s, 2H), 2.70 (d, 2H), 2.55 (s, 3H), 2.42 (s, 3H), 2.30 (d, 1H), 2.21 (m, 1H), 1.50 (s, 3H).

Provenance & Evidence