Boron tribromide → 6-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamide

HRID 1825083Notes

Reaction equation

HRID 1825083 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])[C:6]=1[CH3:17])=[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])[C:6]=1[CH3:17])=[O:4]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 207678696-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid methylamide

Product 1

HCID 221435306-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamideYield 73%

Procedure

Example 16(e) was prepared from 6-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid methylamide 16d (560 mg, 2.4 mmole) by treatment with BBr3 in a manner as previously described for example 1d to obtain 380 mg (73%) of white solid. 1H NMR (DMSO-d6) δ 9.05 (1H, s), 7.50 (1H, d, J=8.59 Hz), 7.35–7.28 (1H, m), 6.73 (1H,d, J=1.77 Hz), 6.60 (1H, dd, J=8.5, 2.27 Hz), 3.54 (3H, s), 2.75 (3H, d, J=4.55 Hz), 2.53 (3H, s). Anal. Calcd. for C12H14N2O2.0.3H2O: C, 64.44; H, 6.58; N, 12.53. Found: C, 64.55; H, 6.49; N, 12.35.

Sources & evidence

ORD record
ord-fca0f185e10445c78937d90e83ed4620
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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