3,4-Dimethoxyphenylboronic acid → HCID 10455700, compound

HRID 1793530Notes

Reaction equation

HRID 1793530 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.[CH3:24][O:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]>>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C:2]2[CH:3]=[C:4]3[C:8]4=[C:9]([CH2:11][CH2:12][N:7]4[C@H:6]4[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:16][C@@H:5]34)[CH:10]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]

Participants

3

Reactant 2

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 20577007Tert-butyl (6aS,10aR)-2-bromo-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6aH)carboxylate

Product 1

HCID 10455700HCID 10455700, compound

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 3,4-dimethoxyphenyl boronic acid (182 mg, 1.0 mmol) to afford after chromatographic purification the title compound (92 mg, 42%). 1H NMR (CDCl3, 300 MHz) δ 7.15 (s, 1H), 7.11(s, 1H), 7.01–7.04 (m, 2H), 6.89 (d, 1H, J=8.0 Hz), 4.02–4.10 (m, 1H), 3.92 (d, 6H, J=8.1 Hz), 3.64–3.78 (m, 1H), 2.82–3.52 (m, 8H), 1.82–1.90 (m, 2H), 1.49 (s, 9H) ppm. MS-ApCI: 437 [M+H+].

Workup

  1. customto afford
  2. customafter chromatographic purification the title compound (92 mg, 42%)

Sources & evidence

ORD record
ord-9243ede4e3bc485695ab85173606d66b
Source dataset
uspto-grants-2006_07
Patent number
US07081455B2

Reaction notes

Loading…