Boron tribromide → 6-Hydroxy-1,2-dimethyl-1H-indol-3-carboxylic acid propylamide

HRID 985253Notes

Reaction equation

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 207678686-Methoxy-1,2-dimethyl-1H-indol-3-carboxylic acid propylamide

Product 1

HCID 221436346-Hydroxy-1,2-dimethyl-1H-indol-3-carboxylic acid propylamide

Procedure

This material was prepared from 6-methoxy-1,2-dimethyl-1H-indol-3-carboxylic acid propylamide 58a by treatment with BBr3 in a manner as previously described for example 1d. 1H NMR (300 MHz, CD3OD) δ7.50 (1H, d, J=8.7 Hz), 6.74 (1H, d, J=1.9 Hz), 6.68 (1H, dd, J=1.9, 8.7 Hz), 3.61 (3H, s), 3.32 (2H, m), 2.58 (3H, s), 1.66 (2H, m), 1.01 (3H, t, J=7.4 Hz). LCMS (ESI+) [M+H]/z Calc'd 247, found 247.

Sources & evidence

ORD record: ord-34df52cd50b84266a16dd481716432e0
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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