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

HRID 985299Notes

Reaction equation

HRID 985299 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.[CH2:20]([NH:24][C:25]([C:27]1[C:31]2[CH:32]=[CH:33][C:34]([OH:36])=[CH:35][C:30]=2[O:29][C:28]=1[CH3:37])=[O:26])[CH:21]([CH3:23])[CH3:22].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:20]([NH:24][C:25]([C:27]1[C:31]2[CH:32]=[CH:33][C:34]([O:36][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:35][C:30]=2[O:29][C:28]=1[CH3:37])=[O:26])[CH:21]([CH3:23])[CH3:22]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677657-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 207678656-Hydroxy-2-methyl-benzofuran-3-carboxylic acid isobutyl amide

Product 1

HCID 207679262-Methyl-6-[2-(3-methoxy-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-benzofuran-3-carboxylic acid isobutyl amide

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-2-methyl-benzofuran-3-carboxylic acid isobutyl amide 83b and Cs2CO3 in a manner as previously described for example 1. 1H NMR (CD3CN) δ8.53 (1H, d, J=5.5 Hz), 7.88 (1H, d, J=3.0 Hz), 7.82 (1H, d, J=8.5 Hz), 7.41 (1H, d, J=2.3 Hz), 7.20 (1H, dd, J=8.5, 2.3 Hz), 6.70 (2H, d, J=5.5 Hz), 4.10-3.83 (3H, m), 3.73-3.58 (2H, m), 3.33, 3.29 (3H, 2s), 3.23 (2H, t, J=6.8 Hz), 2.65 (3H, s), 2.10-1.95 (2H, m), 0.98 (6H, d, J=6.6 Hz).

Sources & evidence

ORD record
ord-5d9c01d524174577b16383477f0d5e11
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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