反应详情

A mixture of 195 (3.00 g, 7.13 mmol), Bu3SnH (2.49 g, 8.55 mmol) and AIBN (120 mg, 0.71 mmol) in benzene (20 mL) was heated under reflux for 1.5 h. The benzene was removed under reduced pressure and the residue was triturated with pentane (×4) and recrystallised (MeOH) to give tert-butyl 1-(chloromethyl)-8-cyano-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (196) (2.24 g, 92%) as colorless needles: mp 138-140° C.; 1H NMR (CDCl3) δ 8.35 (br s, 1H), 8.09 (s, 1H), 7.90 (d, J=8.5 Hz, 1H), 7.82 (d, J=9.0 Hz, 1H), 7.48 (dd, J=8.5, 1.5 Hz, 1H), 430 (br d, J=11.2 Hz, 1H), 4.18 (dd, J=11.8, 8.7 Hz, 1H), 4.50 (tt, J=9.3, 3.0 Hz, 1H), 3.87 (dd, J=−11.3, 3.3 Hz, 1H), 3.53 (dd, J=11.2, 9.6 Hz, 1H), 1.61 (s, 9 M); 13C NMR δ 152.3, 142.9, 131.2, 130.2, 130.0, 128.9, 128.2, 124.2, 123.3, 119.2, 118.8, 110.5, 81.8, 52.8, 462, 41.5, 28.4. Anal. (C19H19ClN2O2) C, H, N.

1. temperaturewas heated
2. temperatureunder reflux for 1.5 h
3. customThe benzene was removed under reduced pressure
4. customthe residue was triturated with pentane (×4)
5. customrecrystallised (MeOH)