Boron tribromide → 6-Hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

HRID 985258Notes

Reaction equation

C[O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=2)[N:11]([CH3:20])[C:10]=1[CH3:21])=[O:8].B(Br)(Br)Br>>[OH:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=2)[N:11]([CH3:20])[C:10]=1[CH3:21])=[O:8]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 865907596-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-methoxy-propyl)-amide

Product 1

HCID 207678646-Hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

Procedure

This material was prepared from 6-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-methoxy-propyl)-amide 63a by treatment with BBr3 in a manner as previously described for example 1d. 1H NMR (300 MHz, CD3OD) δ7.52 (1H, d, J=8.6 Hz), 6.73 (1H, d, J=2.1 Hz), 6.68 (1H, dd, J=2.1, 8.6 Hz), 3.69 (2H, t, J=6.1 Hz), 3.57 (3H, s), 3.51 (2H, m), 2.57 (3H, s), 1.85 (2H, m). LCMS (ESI+) [M+H]/z Calc'd 263, found 263.

Sources & evidence

ORD record: ord-eb263960646f484fb6ede9f4a5d18a16
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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