Boron tribromide → 6-Hydroxy-2-methyl-benzofuran-3-carboxylic acid isobutyl amide
Reaction equation
[CH2:1]([NH:5][C:6]([C:8]1[C:12]2[CH:13]=[CH:14][C:15]([O:17]C)=[CH:16][C:11]=2[O:10][C:9]=1[CH3:19])=[O:7])[CH:2]([CH3:4])[CH3:3].B(Br)(Br)Br>>[CH2:1]([NH:5][C:6]([C:8]1[C:12]2[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:11]=2[O:10][C:9]=1[CH3:19])=[O:7])[CH:2]([CH3:4])[CH3:3]Participants
3
Procedure
This material was prepared from 6-methoxy-2-methyl-benzofuran-3-carboxylic acid isobutyl amide 84a by treatment with BBr3 in a manner as previously described for example 1d. 1H NMR (DMSO-d6) δ 9.53 (1H, s), 7.90 (1H, t, J=6.1 Hz), 7.44 (1H, d, J=8.3 Hz), 6.86 (1H, s), 6.74 (1H, dd, J=8.6, 1.8 Hz), 3.07 (2H, t, J=6.1 Hz), 2.52 (3H, s), 1.81 (1H, m). 0.90 (6H, d, J=6.8 Hz).
Sources & evidence
- ORD record
- ord-cdf0721c97074b2a8b8db44274b00578
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07045528B2
Reaction notes
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