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

HRID 1825089Notes

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]([O:18][CH3:19])[CH2:14]3)=[O:12])[S:10][C:3]=12.[CH3:20][NH:21][C:22]([C:24]1[C:32]2[C:27](=[CH:28][C:29]([OH:33])=[CH:30][CH:31]=2)[N:26]([CH3:34])[CH:25]=1)=[O:23].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:20][NH:21][C:22]([C:24]1[C:32]2[C:27](=[CH:28][C:29]([O:33][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]([O:18][CH3:19])[CH2:14]5)=[O:12])[S:10][C:3]=34)=[CH:30][CH:31]=2)[N:26]([CH3:34])[CH:25]=1)=[O:23]

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 207677657-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine

HCID 235728736-hydroxy-N,1-dimethylindole-3-carboxamide

Product 1

HCID 100959856-[2-(3-methoxypyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-1-methyl-1H-indole-3-carboxylic acid methylamide

Procedure

This material was prepared by the reaction of 7-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 4b with 6-hydroxy-1-methyl-1H-indole-3-carboxylic acid methylamide 21b and Cs2CO3 in a manner as previously described for example 1. 1H NMR (300 MHz, CD3OD) δ 8.53 (1H, d, J=5.5 Hz), 8.25 (1H, d, J=8.7 Hz), 7.96 (1H, d, J=6.2 Hz), 7.86 (1H, s), 7.46 (1H, d, J=1.9 Hz), 7.12 (1H, d, J=8.5 Hz), 6.74 (1H, d, J=5.5 Hz), 4.19–4.11 (1H, m), 4.05–3.95 (2H, m), 3.38 (3H, s), 3.85–3.72 (2H, m), 3.40 (3H, d, J=13.9 Hz), 2.96 (3H, s), 2.30–2.09 (2H, m). LCMS (ESI+) [M+H]/z Calc'd 465. found 465. Anal. (C24H24N4O4S.0.4CH2Cl2) C, H, N.

Sources & evidence

ORD record: ord-8a72cdfedbd5414aa856fe14ca76d0ad
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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