tert-butyl(6bR,10aS)-5-bromo-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate → tert-butyl(6bR,10aS)-5-(2-chloro-6-fluorophenyl)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate

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Reaction Steps

The tert-butyl(6bR,10aS)-5-(2-chloro-6-fluorophenyl)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate (276 mg, 57%) was prepared via coupling tert-butyl(6bR,10aS)-5-bromo-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate (1.0 g, 1.043 mmol) with 2-chloro-6-fluorophenyltrimethyl stannane (3.0 g, 3.129 mmol) as illustrated by the general procedure described in Example 447 Step G. 1H NMR (CDCl3, 300 MHz) δ1.44 (s, 9H), 1.83-1.99 (m, 2H), 2.80-3.32 (m, 5H), 3.33-3.50 (m, 2H), 3.55-3.71 (m, 3H), 6.82 (d, 1H, J=8.1 Hz), 7.01 (t, 1H, J=8.1 Hz), 7.12-7.35 (m, 3H) ppm.

Provenance & Evidence