Cesium carbonate → 2-Methyl-6-[2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid isobutyl amide

HRID 1825180Notes

Reaction equation

HRID 1825180 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]([CH3:16])[CH:13]=[CH:14][N:15]=3)[S:10][C:3]=12.[CH2:17]([NH:21][C:22]([C:24]1[C:28]2[CH:29]=[CH:30][C:31]([OH:33])=[CH:32][C:27]=2[O:26][C:25]=1[CH3:34])=[O:23])[CH:18]([CH3:20])[CH3:19].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:17]([NH:21][C:22]([C:24]1[C:28]2[CH:29]=[CH:30][C:31]([O:33][C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[C:9]([C:11]5[N:12]([CH3:16])[CH:13]=[CH:14][N:15]=5)[S:10][C:3]=34)=[CH:32][C:27]=2[O:26][C:25]=1[CH3:34])=[O:23])[CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207678656-Hydroxy-2-methyl-benzofuran-3-carboxylic acid isobutyl amideHCID 221435637-chloro-2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridine

Product 1

HCID 207679242-Methyl-6-[2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid isobutyl amide

Procedure

This material was prepared by the reaction of 7-chloro-2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridine 1e with 6-hydroxy-2-methyl-benzofuran-3-carboxylic acid isobutyl amide 84b and Cs2CO3 in a manner as previously described for example 1. 1H NMR (CD3CN) δ 8.48 (1H,d, J=5.6 Hz), 7.81 (1H, d, J=8.3 Hz), 7.74 (1H, s), 7.43 (1H, d, J=2.0 Hz), 7.21 (1H, dd, J=8.6, 2.3 Hz), 7.17 (1H, s), 7.04 (1H, s), 6.70 (1H,m), 6.67 (1H, d, J=5.6 Hz), 3.97 (3H, s), 3.23 (2H, t, J=6.6 Hz), 2.66 (3H, s),1.78 (1H,m), 0.98 (6H, d, J=6.6 Hz).

Sources & evidence

ORD record
ord-934455cf90ce419eb5b91b59d961e41f
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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