Cesium carbonate → 6-[2-(3-Hydroxy-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-2-methyl-1H-indole-3-carboxylic acid methylamide
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14]3)=[O:12])[S:10][C:3]=12.[CH3:19][NH:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][C:28]([OH:32])=[CH:29][CH:30]=2)[NH:25][C:24]=1[CH3:33])=[O:22].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:19][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]([N:13]5[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14]5)=[O:12])[S:10][C:3]=34)=[CH:29][CH:30]=2)[NH:25][C:24]=1[CH3:33])=[O:22]Participants
4
Reactant 3
Product 1
Procedure
This material was prepared by the reaction of 7-chloro-2-[(R)-3-hydroxypyrrolidine-1-carbynyl]thieno[3,2,-b]pyridine 4a with 6-hydroxy-2-methyl-1H-indol-3-carboxylic acid methylamide and Cs2CO3 in a manner as previously described for Example 1. 1H NMR (300 MHz, CD3OD) δ8.48 (1H, d, J=5.5 Hz), 7.91 (1H, d, J=17.3 Hz), 7.86 (1H, d, J=8.6 Hz), 7.21 (1H, s), 7.00 (1H, d, J=8.6 Hz), 6.69 (1H, d, J=5.5 Hz), 4.50 (1H, m), 4.05-3.70 (4H, m), 2.97 (3H, s), 2.63 (3H, s), 2.40-1.90 (2H, m). LCMS (ESI+) [M+H]/z Calc'd 451, found 451.
Sources & evidence
- ORD record
- ord-ea7672116b4b44669fd4cec72ef14042
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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