Tributylstannane → HCID 44550374, compound

Participants

Reaction Steps

A mixture of 163 (5.38 g, 11.33 mmol), Bu3SnH (3.05 mL, 11.34 mmol) and AIBN (0.25 g, 1.5 mmol) in dry benzene (80 mL) under N2 was stirred at reflux for 2 h, then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 and the solution was diluted with excess hexane and refrigerated. The precipitated semisolid was purified by chromatography on silica gel, eluting with CH2Cl2/EtOAc (19:1), to give tert-butyl 1-(chloromethyl)-7-(methylsulfonyl)-1,2-dihydro-3H-benzo[e]indole 3-carboxylate (164) (3.53 g, 79%) as a white solid: mp (iPr2O) 125-126° C.; 1H NMR [(CD3)2SO] δ 8.54 (d, J=1.8 Hz, 1H), 8.25-8.05 (m, 3H), 7.91 (dd, J=8.9, 1.9 Hz, 1H), 4.36-4.27 (m, 1H), 4.23 (t, f=10.5 Hz, 1H), 4.10 (dd, J=11.4, 2.9 Hz, 1H), 4.05 (dd, J=11.1, 3:2 Hz, 1H), 3.94 (dd, J=11.1, 6.7 Hz, 1H, 3.21 (after D2O exchange, s, 3H, 1.56 (s, 9H). Anal. (C19H22ClNO4S) C, H, N.

Provenance & Evidence