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-(2-isopropyl-4-methoxyphenyl)-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate

HRID 1793533Notes

Reaction equation

HRID 1793533 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8]3=[C:9]([CH2:11][CH2:12][N:7]3[C@H:6]3[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C@@H:5]23)[CH:10]=1.[CH:24]([C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=1B(O)O)([CH3:26])[CH3:25]>>[CH:24]([C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=1[C:2]1[CH:3]=[C:4]2[C:8]3=[C:9]([CH2:11][CH2:12][N:7]3[C@H:6]3[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:16][C@@H:5]23)[CH:10]=1)([CH3:26])[CH3:25]

Participants

3

Reactant 2

HCID 20577007Tert-butyl (6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylateHCID 220217692-Isopropyl-4-methoxyphenyl boronic acid

Product 1

HCID 10026690tert-butyl (6aS,10aR)-2-(2-isopropyl-4-methoxyphenyl)-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)-carboxylate

Procedure

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 2-isopropyl-4-methoxyphenyl boronic acid (178 mg, 1.0 mmol) to afford after chromatographic purification the title compound (152 mg, 68%). 1H NMR (CDCl3, 300 MHz) δ 7.09 (d, 1H, J=8.4 Hz), 6.88 (d, 1H, J=2.5 Hz), 6.83 (s, 1H), 6.78 (s, 1H), 6.72 (dd, 1H, J=8.4, 2.9 Hz), 3.80–4.20 (m, 2H), 3.84 (s, 3H), 3.74–3.78 (m, 1H), 3.05–3.50 (m, 7H), 2.84–2.98 (m, 1H), 1.82–1.94 (m, 2H), 1.48 (s, 9H), 1.12–1.17 (m, 6H) ppm. MS-ApCI: 449. [M+H+].

Workup

  1. customto afford
  2. customafter chromatographic purification the title compound (152 mg, 68%)

Sources & evidence

ORD record
ord-7c89020e55a54e6f82b3630ecff61c78
Source dataset
uspto-grants-2006_07
Patent number
US07081455B2

Reaction notes

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