Cesium carbonate → N,2-Dimethyl-6-(thieno[3,2-b]pyridin-7-yloxy)-3-benzofurancarboxamide

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[CH3:11][NH:12][C:13]([C:15]1[C:19]2[CH:20]=[CH:21][C:22]([OH:24])=[CH:23][C:18]=2[O:17][C:16]=1[CH3:25])=[O:14].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:11][NH:12][C:13]([C:15]1[C:19]2[CH:20]=[CH:21][C:22]([O:24][C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[CH:9][S:10][C:3]=34)=[CH:23][C:18]=2[O:17][C:16]=1[CH3:25])=[O:14]

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 112752517-Chlorothieno[3,2-b]pyridine

HCID 167551736-Hydroxy-N,2-dimethylbenzofuran-3-carboxamide

Product 1

HCID 20767890N,2-Dimethyl-6-(thieno[3,2-b]pyridin-7-yloxy)-3-benzofurancarboxamide

Procedure

This material was prepared by the reaction of 7-chloro-thieno[3,2-b]pyridine with 6-hydroxy-2-methylbenzofuran-3-carboxylic acid methyl amide 12c and Cs2CO3 in a manner as previously described for example 1. 1H NMR (CD3CN) δ 8.48 (1H,d, J=5.3 Hz), 7.91 (1H, d, J=5.6 Hz), 7.84 (1H, d, J=8.6 Hz), 7.53 (1H, d, J=5.6 Hz), 7.41 (1H, d, J=2.0 Hz), 7.20 (1H, dd, J=8.6, 2.0 Hz), 6.62 (1H, d, J=5.3 Hz), 6.60 (1H, bm), 2.91 (3H, d, J=4.6 Hz) 2.66 (3H, s).