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-(5-fluoro-4-methoxy-2-methylphenyl)-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 corresponding 5-fluoro-4-methoxy-2-methylphenyl boronic acid (184 mg, 1.0 mmol) to afford after chromatographic purification the title compound (130 mg, 60%). 1H NMR (CDCl3, 300 MHz) δ 6.94 (d, 1H, J=12.5 Hz), 6.84 (s, 1H), 6.79–6.82 (m, 2H), 4.02–4.22 (m, 1H), 3.90 (s, 311), 3.82–3.92 (m, 1H), 3.64–3.74 (m, 1H), 3.24–3.54 (m, 4H), 2.86–3.22 (m, 3H), 2.22 (s, 3H), 1.82–1.94 (m, 2H), 1.48 (s, 9H) ppm. MS-ApCI: 439 [M+H+].

Provenance & Evidence