Boron tribromide → 6-Hydroxy-2-methyl-1H-indol-3-carboxylic acid methylamide

HRID 1825092Notes

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)[NH:7][C:6]=1[CH3:16])=[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)[NH:7][C:6]=1[CH3:16])=[O:4]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 207678716-Methoxy-2-methyl-1H-indol-3-carboxylic acid methylamide

Product 1

HCID 207678626-Hydroxy-2-methyl-1H-indol-3-carboxylic acid methylamide

Procedure

This material was prepared from 6-methoxy-2-methyl-1H-indol-3-carboxylic acid methylamide 24a by treatment with BBr3 in a manner as previously described for example 1d. 1H NMR (300 MHz, CD3OD) δ 7.52 (1H, d, J=8.7 Hz), 6.72 (1H, d, J=2.3 Hz), 6.65 (1H, dd, J=2.3, 8.7 Hz), 2.93 (3H, s), 2.55 (3H, s). LCMS (ESI+) [M+H]/z Calc'd 205. found 205.

Sources & evidence

ORD record: ord-f77e79c002204889a7227f832d4676dd
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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