Cesium carbonate → 2-Ethyl-1-methyl-6-[2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridin-7-yloxy]-1H-indole-3-carboxylic acid methylamide

Reaktionsgleichung

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]([C:19]1[N:20]([CH3:33])[C:21]2[C:26]([C:27]=1[C:28]([NH:30][CH3:31])=[O:29])=[CH:25][CH:24]=[C:23]([OH:32])[CH:22]=2)[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:31][NH:30][C:28]([C:27]1[C:26]2[C:21](=[CH:22][C:23]([O:32][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:24][CH:25]=2)[N:20]([CH3:33])[C:19]=1[CH2:17][CH3:18])=[O:29]

Komponenten

Edukt 3

HCID 10796Cesium carbonate

HCID 221435637-chloro-2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridine

HCID 221436512-ethyl-6-hydroxy-N,1-dimethyl-1H-indole-3-carboxamide

Produkt 1

HCID 207677962-Ethyl-1-methyl-6-[2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridin-7-yloxy]-1H-indole-3-carboxylic acid methylamideAusbeute 40 %

Versuchsvorschrift

This material was prepared by the reaction 7-chloro-2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridine 1e (0.084 g, 0.34 mmole) with 2-ethyl-6-hydroxy-N,1-dimethyl-1H-indole-3-carboxamide 73 g (0.078 g, 0.33 mmole) and Cs2CO3 (0.111 g, 0.34 mmole) in a manner as previously described for example 1 to give an off-white solid (0.058 g, 40%). 1H NMR (300 MHz, CD3OD 67 8.27 (1H, d, J=5.4 Hz), 7.68 (1H, d, J=8.6 Hz), 7.59 (1H, s), 7.24 (1H, d, J=1.9 Hz), 7.17 (1H, s), 6.96 (1H, s), 6.90 (1H, dd, J=1.9, 8.6 Hz), 6.50 (1H, d, J=5.4 Hz), 3.87 (3H, s), 3.58 (3H, s), 3.01 (2H, m), 2.85 (3H, s), 1.14 (3H, m). HRMS (MH+): Calcd: 446.1655; Found: 446.1651.