Cesium carbonate → 6-(2-[(S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yloxy)-2-methyl-benzofuran-3-carboxylic acid methyl amide

HRID 1825176Notes

Reaction equation

HRID 1825176 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][CH2:15][C@H:14]3[CH2:18][O:19][CH3:20])=[O:12])[S:10][C:3]=12.[CH3:21][NH:22][C:23]([C:25]1[C:29]2[CH:30]=[CH:31][C:32]([OH:34])=[CH:33][C:28]=2[O:27][C:26]=1[CH3:35])=[O:24].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:21][NH:22][C:23]([C:25]1[C:29]2[CH:30]=[CH:31][C:32]([O:34][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][CH2:15][C@H:14]5[CH2:18][O:19][CH3:20])=[O:12])[S:10][C:3]=34)=[CH:33][C:28]=2[O:27][C:26]=1[CH3:35])=[O:24]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 167551736-Hydroxy-N,2-dimethylbenzofuran-3-carboxamideHCID 207677647-chloro-2-[(S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine

Product 1

HCID 599907606-(2-[(S)-2-(methoxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yloxy)-2-methyl-benzofuran-3-carboxylic acid methyl amide

Procedure

This material was prepared by the reaction of 7-chloro-2-[(R)-2-methoxymethylpyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 2a with 6-Hydroxy-2-methyl-benzofuran-3-carboxylic acid methyl amide 12c and Cs2CO3 in a manner as previously described for example 1. 1H NMR (DMSO-d6) δ 8.57 (1H,d, J=5.3 Hz), 8.02 (1H, s),7.98 (1H, m), 7.83 (1H, d, J=8.6 Hz), 7.66 (1H, d, J=2.0 Hz), 7.25 (1H, dd, J=8.6, 2.0 Hz), 6.72 (1H, d, J=5.3 Hz), 4.31 (1H,m), 3.94–3.80 (2H, m), 3.60–3.39 (2H, m), 3.28 (3H, s), 2.82 (3H, d, J=4.6 Hz), 2.63 (3H, s), 2.06–1.85 (4H,m).

Sources & evidence

ORD record
ord-a42395d40da9425eb63e1f82d4cab6f3
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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