(3-Methoxyphenyl)boronic acid → HCID 22032965, compound

HRID 2221260Notes

Reaction equation

HRID 2221260 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[CH:6]=[CH:5]2.[CH3:22][O:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1>>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH3:22])[CH:25]=4)=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)=[CH:13][CH:14]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

3

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 21964287HCID 21964287, compound

Product 1

HCID 22032965HCID 22032965, compound

Procedure

The title compound was prepared from 5-bromo-1-[4-(tert-butyl)benzyl]-1H-indole (Step 1 of Example 34) and 3-methoxyphenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 370. 1HNMR (400 MHz, DMSO-d6): δ 7.81 (s, 1H), 7.53 (s, 1H), 7.51 (d, 1H, J=8.55 Hz), 7.39 (d, 1H, J=8.55 Hz), 7.34-7.30 (m, 3H), 7.20 (d, 1H, J=7.64 Hz), 7.15-7.13 (m, 3H), 6.85 (d, 1H, J=8.25 Hz), 6.52 (d, 1H, J=3.05 Hz), 5.39 (s, 2H), 5.81 (s, 3H), and 1.21 ppm (s, 9H). Elemental Analysis for C26H27NO: Calculated: C, 84.51; H, 7.37; N, 3.79. Found: C, 83.30; H, 7.42; N, 3.74.

Workup

  1. customThe product was obtained as an oil

Sources & evidence

ORD record
ord-cc04c9f9de804557b23307ca3dda7944
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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