Tributylstannane → HCID 44550495, compound

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[N:16]([CH2:24][CH:25]=[CH:26][Cl:27])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].CCCC[SnH](CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[Cl:27][CH2:26][CH:25]1[C:2]2[C:11]3[CH:10]=[C:9]([S:12]([CH3:15])(=[O:13])=[O:14])[CH:8]=[CH:7][C:6]=3[CH:5]=[CH:4][C:3]=2[N:16]([C:17]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:23])[CH2:24]1

Participants

Procedure

A solution of 204 (1.60 g, 3.37 mmol) in dry benzene (30 mL) was treated with Bu3SnH (0.91 mL, 3.38 mmol) followed by AIBN (0.1 g, 0.6 mmol). The mixture was stirred under N2 at reflux for 2 h, then concentrated under reduced pressure. The residue was dissolved in EtOAc, and the solution was diluted with hexane and refrigerated. The resulting semisolid was chromatographed on silica gel, eluting with CH2Cl2/EtOAc (19:1), and the product was triturated with i-Pr2O/hexane to give tert-butyl 1-(chloromethyl)-8-(methylsulfonyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (205) (0.88 g, 66%) as an amorphous solid: 1H NMR [(CD3)2SO] δ 8.41 (d, J=1.6 Hz, 1H), 8.2 (v br, 1H), 8.17 (d, J=8.6 Hz, 1H), 8.03 (d, J=8.9. Hz. H), 7.80 (dd, J=8.6, 1.8 Hz, 1H), 4.42-4.33 (m, 1H), 4.21 (t, J=10.4 Hz, 1H), 4.12 (dd, J=11.6, 2.9 Hz, 1H), 4.07 (dd, J=11.2, 3.4 Hz, 1H). 3.89 (dd, J=11.2, 7.1 Hz; 1H), 3.33 (s, 3H), 1.55 (s, 9H). Anal. (C19H22ClNO4S.½i-Pr2O) C, H, N.