(3-Methoxyphenyl)boronic acid → HCID 22032902, compound

HRID 2221255Notes

Reaction equation

HRID 2221255 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][CH3:14])[CH:6]=[CH:5]2.[CH3:15][O:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1>>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([O:16][CH3:15])[CH:22]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6]1)[CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 131691555-Bromo-1-butyl-1H-indole

Product 1

HCID 22032902HCID 22032902, compound

Procedure

The title compound was prepared from 5-bromo-1-butyl-1H-indole (Step 1 of Example 29) 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 (APCI, [M+H]+) m/z 280. 1HNMR (300 MHz, DMSO-d6): δ 7.81 (s, 1H), 7.52 (d, 1H, J=8.30 Hz), 7.43-7.38 (m, 2H), 7.39(dd, 1H, J=7.70 and 7.91 Hz), 7.22 (d, 1H, J=8.50 Hz), 7.17 (s, 1H), 6.85 (d, 1H, J=7.10 Hz), 6.46 (d, 1H, J=3.05 Hz), 4.18 (t, 2H, J=7.01 Hz), 3.81 (s, 3H), 1.73 (p, 2H, J=7.16 Hz), 1.25 (h, 2H, J=7.46 Hz), and 0.87 ppm (t, 3H, J=7.31 Hz). Elemental Analysis for C19H21NO: Calculated: C, 76.18; H, 6.39; N, 4.94. Found: C, 76.85; H, 6.23; N, 4.81.

Workup

  1. customThe product was obtained as an oil

Sources & evidence

ORD record
ord-8b148236bbfe4c758ca0b5fca1bab96b
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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