Cesium carbonate → tert-butyl (3R)-1-{[7-({1,2-dimethyl-3-[(methylamino)carbonyl]-1H-indol-6-yl}oxy)thieno[3,2-b]pyridin-2-yl]carbonyl}pyrrolidin-3-yl(methyl)carbamate
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]([N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14]3)=[O:12])[S:10][C:3]=12.[CH3:27][NH:28][C:29]([C:31]1[C:39]2[C:34](=[CH:35][C:36]([OH:40])=[CH:37][CH:38]=2)[N:33]([CH3:41])[C:32]=1[CH3:42])=[O:30].C([O-])([O-])=O.[Cs+].[Cs+]>>[C:21]([O:20][C:19](=[O:25])[N:18]([C@@H:15]1[CH2:16][CH2:17][N:13]([C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[O:40][C:36]3[CH:35]=[C:34]4[C:39]([C:31]([C:29]([NH:28][CH3:27])=[O:30])=[C:32]([CH3:42])[N:33]4[CH3:41])=[CH:38][CH:37]=3)[CH:8]=2)=[O:12])[CH2:14]1)[CH3:26])([CH3:24])([CH3:23])[CH3:22]Participants
Reactant 3
Product 1
Procedure
This material was prepared by the reaction of tert-butyl (3R)-1-[(7-chlorothieno[3,2-b]pyridin-2-yl)carbonyl]pyrrolidin-3-yl(methyl)carbamate 34c (0.181 g, 0.46 mmole) with 6-hydroxy-N,1,2-trimethyl-1H-indole-3-carboxamide 16e (0.10 g, 0.46 mmole) and Cs2CO3 (0.149 g, 0.46 mmole) in a manner as previously described for example 1 to give a yellow solid (0.105 g, 40%). 1H NMR (300 MHz, CDCl3) δ8.48 (1H, d, J=5.4 Hz), 7.82 (1H, s), 7.75 (1H, d, J=8.7 Hz), 7.15 (1H, d, J=2.1 Hz), 7.02 (1H, dd, J=2.1, 8.7 Hz), 6.56 (1H, d, J=5.4 Hz), 5.91 (1H, d, J=4.7 Hz), 4.82 (1H, m), 4.07 (2H, m), 3.87 (1H, m), 3.68 (1H, m), 3.65 (3H, s), 3.05 (3H, d, J=4.7 Hz), 2.84 (3H, s), 2.73 (3H, s), 2.17 (2H, m), 1.45 (9H, s); HRMS (MH+): Calcd: 578.2450; Found: 578.2437.
Sources & evidence
- ORD record
- ord-d3377866e04b461384c4dcc134281896
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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