Boron tribromide → 2-Ethyl-6-[2-(3-hydroxy-pyrrol idine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid methylamide
Reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]([N:26]5[CH2:30][CH2:29][CH:28]([O:31]C)[CH2:27]5)=[O:25])[S:23][C:16]=34)=[CH:13][C:8]=2[O:7][C:6]=1[CH2:33][CH3:34])=[O:4].B(Br)(Br)Br.CNC(C1C2C=CC(O)=CC=2SC=1C)=O>>[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]([N:26]5[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27]5)=[O:25])[S:23][C:16]=34)=[CH:13][C:8]=2[O:7][C:6]=1[CH2:33][CH3:34])=[O:4]Participants
4
Reactant 3
Product 1
Procedure
This material was prepared from 2-ethyl-6-[2-(3-methoxypyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]benzofuran-3-carboxylic acid methylamide 14 by treatment with BBr3 in a manner as previously described for 1d. 1H NMR (DMSO-d6) δ 8.56 (1H, d, J=5.3 Hz), 8.07(1H, s), 8.00 (1H, d, J=4.1 Hz), 7.82 (1H, d, J=8.6 Hz), 7.68 (1H, d, J=2.0 Hz), 7.25 (1H, dd, J=8.6, 2.0 Hz), 6.73 (1H, d, J=5.3 Hz), 5.07 (1H, t, J=3.5 Hz), 4.35 (1H, m), 3.97 (1H, m), 3.86–3.46 (3H, m), 3.03 (2H, q, J=7.6 Hz), 2.80 (3H, d, J=4.5 Hz), 2.10–1.80 (2H, m), 1.27 (3H, t, J=7.6 Hz).
Sources & evidence
- ORD record
- ord-f7e63e954d864fa0a32c0c04865dd192
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07045528B2
Reaction notes
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