Tributylstannane → methyl 3-(tert-butoxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indole-7-carboxylate

Participants

Reaction Steps

A mixture of 149 (1.16 g, 2.55 mmol), Bu3SnH (0.69 mL, 2.56 mmol) and AIBN (50 mg, 0.30 mmol) in dry benzene (15 mL) under N2 was stirred at reflux for 2 h, then concentrated under reduced pressure. The residue was triturated with i-Pr2O and the resulting solid was purified by chromatography on silica gel, eluting with CH2Cl2/EtOAc (19:1), to give methyl 3-(tert-butoxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indole-7-carboxylate (150) (817 mg, 85%) as a white solid. mp EtOAc) 187-189° C.; 1H NMR [(CD3)2SO] δ 8.60 (d, J=1.2 z, 1H), 8.1 (v br, 1H), 8.09 (d, J=8.6 Hz, 1H), 8.00 (d, J=8.8 Hz, 1H), 7.97 (dd, J=8.8, 1.6 Hz, 1H), 4.31-4.23 (m, 1H), 4.20 (t, J=10.4 Hz, 1H), 4.09 (dd, J=11.2, 2.5 Hz, 1H), 4.04 (dd, J=11.1, 3.1 Hz, 1H), 3.96-3.88 (m, 4H), 1.55 (s, 9H). Anal. (C20H22ClNO4) C, H, N.

Provenance & Evidence