Cesium carbonate → 1,2-Dimethyl-6-[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy]-1H-indole-3-carboxylic acid propylamide
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:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][C:28]([OH:32])=[CH:29][CH:30]=2)[N:25]([CH3:33])[C:24]=1[CH3:34])=[O:22])[CH2:18][CH3:19].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:17]([NH:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][C:28]([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:29][CH:30]=2)[N:25]([CH3:33])[C:24]=1[CH3:34])=[O:22])[CH2:18][CH3:19]Participants
4
Reactant 3
Product 1
Procedure
This material was prepared from 7-chloro-2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridine 1e with 6-hydroxy-1,2-dimethyl1H-indole-3-carboxylic acid propylamide 58b and Cs2CO3 in a manner as previously described for example 1. 1H NMR (300 MHz, CDCl3) δ8.42 (1H, d, J=5.5 Hz), 7.82 (1H, d, J=8.7 Hz), 7.76 (1H, s), 7.37 (1H, d, J=1.8 Hz), 7.30 (1H, s), 7.08 (1H, s), 7.03 (1H, dd, J=1.8, 8.7 Hz), 6.65 (1H, d, J=5.5 Hz), 4.01 (3H, s), 3.70 (3H, s), 3.39 (2H, m), 2.64 (3H, s), 1.70 (2H, m), 1.03 (3H, m). LCMS (ESI+) [M+H]/z Calc'd 460, found 460.
Sources & evidence
- ORD record
- ord-0e6cd9705738472bb242acc90e3f58df
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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