Tert-butyl (6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate → tert-butyl (6aS,10aR)-2-[4-isopropoxy-2-(trifluoromethyl)phenyl]-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate

Participants

Reaction Steps

The title compound was prepared by the method of Example 89 step C from tert-butyl(6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate (189 mg, 0.5 mmol) and 4-isopropoxy-2-(trifluoromethyl)phenylboronic acid (248 mg, 1.0 mmol) to afford after chromatographic purification the title compound (186 mg, 74%). 1H NMR (CDCl3, 300 MHz) δ 7.11–7.18 (m,2H), 6.90–6.94 (m, 1H), 6.78 (s, 1H), 6.74 (s, 1H), 4.50–4.54 (m, 1H), 3.75–3.85 (m, 1H), 3.59–3.70 (m, 1H), 2.79–3.40 (m, 8H), 1.74–1.84 (m, 2H), 1.40 (s, 9H), 1.21 (d, 6H, J=5.9 Hz) ppm. MS-ApCI: 503 [M+H+].

Provenance & Evidence