Boron tribromide → 2-Methyl-6-[2-(2-hydroxymethyl-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid isobutyl amide

HRID 985298Notes

Reaction equation

[CH2:1]([NH:5][C:6]([C:8]1[C:12]2[CH:13]=[CH:14][C:15]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[CH:24]=[C:25]([C:27]([N:29]5[CH2:33][CH2:32][CH2:31][CH:30]5[CH2:34][O:35]C)=[O:28])[S:26][C:19]=34)=[CH:16][C:11]=2[O:10][C:9]=1[CH3:37])=[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]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[CH:24]=[C:25]([C:27]([N:29]5[CH2:33][CH2:32][CH2:31][CH:30]5[CH2:34][OH:35])=[O:28])[S:26][C:19]=34)=[CH:16][C:11]=2[O:10][C:9]=1[CH3:37])=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 207679252-Methyl-6-[2-(2-methoxymethyl-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid isobutyl amide

Product 1

HCID 207678192-Methyl-6-[2-(2-hydroxymethyl-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid isobutyl amide

Procedure

This material was prepared from 2-methyl-6-[2-(2-methoxymethyl-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid isobutyl amide 85 by treatment with BBr3 in a manner as previously described for example 1d. 1H NMR (CD3CN) δ8.52 (1H, d, J=5.5 Hz), 7.89 (1H, s), 7.81 (1H, d, J=8.5 Hz), 7.42 (1H, d, J=2.1 Hz), 7.20 (1H, dd, J=8.5, 2.1 Hz), 6.78 (1H, m), 6.71 (1H, d, J=5.3 Hz), 4.29 (1H, m), 3.94-3.63 (4H, m), 3.22 (2H, t, J=6.4 Hz), 2.65 (3H, s), 2.22-1.95 (4H, m), 0.98 (6H, d, J=6.8 Hz).

Sources & evidence

ORD record: ord-3d4527465dbd493596c2a35e64163b30
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869962B2

Reaction notes

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