Indole → 1H-indole-1-propionamide

HRID 1771070Notes

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][CH2:12][C:13]([NH2:15])=[O:14]>>[N:1]1([CH2:11][CH2:12][C:13]([NH2:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

Reactant 2

HCID 798Indole

HCID 2335893-Bromopropionamide

Product 1

HCID 887551H-indole-1-propionamide

Procedure

The title compound was prepared from 1H-indole (0.500 g, 4.27 mmol) and 3-bromopropanamide (0.650 g, 4.27 mmol) following a procedure similar to General Procedure A. The title compound was purified by preparatory HPLC method 1 and isolated as a white solid (0.339 g, 42%). 1H NMR (400 MHz, MeOD): δ 7.53 (d, J=7.9 Hz, 1H), 7.44 (d, J=8.3 Hz, 1H), 7.19 (d, J=2.9 Hz, 1H), 7.16 (t, J=7.5 Hz, 1H), 7.03 (t, J=7.4 Hz, 1H), 6.42 (d, J=2.8 Hz, 1H), 4.47 (t, J=6.8 Hz, 2H), 2.70 (t, J=6.8 Hz, 2H). 13C NMR (100 MHz, DMSO-d6): δ 172.4, 135.9, 129.0, 128.6, 121.4, 120.8, 119.4, 110.2, 101.0, 42.3, 36.2. ESI-LRMS: [M+H]+=189.1 m/z. ESI-HRMS: calc. for C11H12N2O1: [M+H]+=189.1022 m/z, found: [M+H]+=189.1030 m/z.

Workup

customThe title compound was purified by preparatory HPLC method 1

Sources & evidence

ORD record: ord-5ba1a9030f954375ad7623d5bf5bce33
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249087B2

Reaction notes

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