(3-Chlorophenyl)boronic acid → HCID 22032919, compound

HRID 2221264Notes

Reaction equation

HRID 2221264 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.[Cl:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1>>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([C:27]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:22])[CH:28]=4)=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)=[CH:17][CH:16]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 21964287HCID 21964287, compound

Product 1

HCID 22032919HCID 22032919, compound

Procedure

The title compound was prepared from 5-bromo-1-[4-(tert-butyl)benzyl]-1H-indole (Step 1 of Example 34) and 3-chlorophenylboronic 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 374. 1HNMR (400 MHz, DMSO-d6): δ 7.86 (d, 1H, J=1.53 Hz), 7.68 (dd, 1H, J=1.84 and 1.83 Hz), 7.61 (d, 1H, J=7.79 Hz), 7.43 (d, 1H, J=8.40 Hz), 7.36 (d, 1H, J=8.55 Hz), 7.55-7.54 (m, 2H), 7.46-7.41 (m, 2H), 7.34 (d, 1H, J=1.07 Hz), 7.31 (d, 2H, J=8.40 Hz), 7.13 (d, 2H, J=8.40 Hz), 6.53 (d, 1H, J=3.06 Hz), 5.40 (s, 2H), 1.30 (s, 9H), and 1.21 ppm (s, 9H). Elemental Analysis for C26H27NO: Calculated: C, 84.51; H, 7.37; N, 3.79. Found: C, 85.08; H, 7.35; N, 3.66.

Workup

  1. customThe product was obtained as an oil

Sources & evidence

ORD record
ord-6e160f9f246c46478369cfbdc8fa42a2
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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