4-Bromo-1,2-dichlorobenzene → (7bR,11aS)-N-(3,4-dichlorophenyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-amine

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Using 3,4-dichloro-1-bromobenzene and following the procedures described in EXAMPLE 33, Parts C and D, tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indole-9(8H)-carboxylate from EXAMPLE 33, Part B was converted into the title compound of EXAMPLE 39 as a powder. 1H NMR(CDCl3, 300 MHz) δ 1.82-1.87 (m, 2H), 2.48-2.55 (m, 1H), 2.57-2.64 (m, 1H), 2.81-3.13 (m, 6H), 3.18-3.25 (m, 1H), 3.42-3.47 (m, 1H), 3.57-3.64 (m, 1H), 3.72 (s, 2H), 5.55 (s, 1H), 6.61-6.68 (m, 2H), 6.74 (s, 1H), 6.89 (d, 1H, J=3 Hz), 7.19 (d, 1H, J=9 Hz). LRMS (ES)+: 406 (M+H)+.

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