Boron tribromide → 6-hydroxy-N,1-dimethylindole-3-carboxamide

HRID 985211Notes

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]([CH3:16])[CH:6]=1)=[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]([CH3:16])[CH:6]=1)=[O:4]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 221434906-methoxy-N,1-dimethyl-1H-indole-3-carboxamide

Product 1

HCID 235728736-hydroxy-N,1-dimethylindole-3-carboxamideYield 51.1%

Procedure

This material was prepared from 6-methoxy-1-methyl-1H-indole-3-carboxylic acid methylamide 21a (453 mg, 2.1 mmol) by treatment with BBr3 in a manner as previously described for example 1d to give 219 mg (51%) of a pale orange solid. 1H NMR (CD3OD) δ7.75 (1H, d, J=8.5 Hz), 7.47 (1H, s), 6.61-6.66 (2H, m), 3.62 (3H, s), 3.24 (1H, s), 2.79 (3H, s). ESIMS (MH+): 205.10.

Sources & evidence

ORD record: ord-ea232dacefcb428d8d5f29a93728cdad
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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