Indole → HCID 60164617, compound

HRID 1771069Notes

Reaction equation

HRID 1771069 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=1>>[N:1]1([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

3

Reactant 2

HCID 798IndoleHCID 5837851-[4-(Bromomethyl)phenyl]ethan-1-one

Product 1

HCID 60164617HCID 60164617, compound

Procedure

The title compound was prepared from 1H-indole (0.55 g, 4.69 mmol) and 1-(4-(bromomethyl)phenyl)ethanone (1.00 g, 4.69 mmol) following a procedure similar to General Procedure A. The title compound was purified using automated column chromatography method 1 (0.410 g, 35%). 1H NMR (400 MHz, CDCl3): δ 7.90 (d, J=8.2 Hz, 2H), 7.69 (d, J=7.5 Hz, 1H), 7.21 (m, 6H), 6.61 (d, J=3.1 Hz, 1H), 5.41 (s, 2H), 2.58 (s, 3H). 13C NMR (100 MHz, MeOD): δ 198.58, 143.95, 136.22, 136.04, 128.94, 128.39, 128.17, 126.51, 121.19, 120.37, 119.06, 109.29, 101.24, 48.95, 25.23. ESI-HRMS: calc. for C17H15NO: [M+H]+=250.1226 m/z, found: [M+H]+=250.1232 m/z.

Workup

  1. customThe title compound was purified

Sources & evidence

ORD record
ord-753386e6db9d4e1e878ee169537ecdf8
Source dataset
uspto-grants-2016_02
Patent number
US09249087B2

Reaction notes

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