Boron tribromide → HCID 20767781, compound

HRID 1825155Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14]C)=[CH:11][CH:12]=2)[N:7]([CH2:16][CH3:17])[C:6]=1[CH3:18])=[O:4].B(Br)(Br)Br>>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:14])=[CH:11][CH:12]=2)[N:7]([CH2:16][CH3:17])[C:6]=1[CH3:18])=[O:4]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 20767782HCID 20767782, compound

Product 1

HCID 20767781HCID 20767781, compoundYield 85%

Procedure

This material was prepared from 1-ethyl-6-methoxy-2-methyl-1H-indole-3-carboxylic acid methylamide 71d (350 mg, 1.42 mmole) by treatment with BBr3 in a manner as previously described for example 1d to give 280 mg product as white solid (85% yield). 1H NMR (400 MHz, CDCl3) δ 7.48 (1H, d, J=8.3 Hz), 6.73–6.77 (2H, m), 6.01 (1H, bs), 4.04 (2H, q, J=7.2 Hz, 3.03 (3H, d, J=4.9 Hz), 2.66 (3H, s), 1.31 (3H, t, J=7.2 Hz).

Sources & evidence

ORD record: ord-1e415c48d9f043279431352e9060a98c
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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