Boron tribromide → 1,2-dimethyl-6-hydroxy-1H-indole-3-carboxylic acid cyclopropylamide

HRID 985209Notes

Reaction equation

[CH:1]1([NH:4][C:5]([C:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16]C)=[CH:13][CH:14]=3)[N:9]([CH3:18])[C:8]=2[CH3:19])=[O:6])[CH2:3][CH2:2]1.B(Br)(Br)Br>>[CH:1]1([NH:4][C:5]([C:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[N:9]([CH3:18])[C:8]=2[CH3:19])=[O:6])[CH2:2][CH2:3]1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 207679146-Methoxy-1,2-dimethyl-1H-indol-3-carboxylic acid cyclopropylamide

Product 1

HCID 221435471,2-dimethyl-6-hydroxy-1H-indole-3-carboxylic acid cyclopropylamideYield 21.3%

Procedure

This material was prepared from 6-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid cyclopropylamide 20a (655 mg, 2.5 mmole) by treatment with BBr3 in a manner as previously described for example 1d to give 130 mg (21%) of a white solid. 1H NMR (DMSO-d6) δ9.06 (1H, s), 7.51 (1H, d, J=4.0 Hz), 7.41 (1H, d, J=8.5 Hz), 6.73 (1H, d, J=1.8 Hz), 6.60 (1H, dd, J=1.8, 8.5 Hz), 3.56 (3H, s), 2.82 (1H, m), 2.50 (3H, s), 0.62 (2H, m), 0.52 (2H, m).

Sources & evidence

ORD record: ord-d140c783032942dfb4a820a9d2f8d860
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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