Cesium carbonate → 2-Ethyl-6-[(2-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]benzo[b]thiophene-3-carboxylic acid methylamide

HRID 985342Notes

Reaction equation

HRID 985342 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:25]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:26]=2[S:27][C:28]=1[CH2:29][CH3:30])=[O:23].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:20][NH:21][C:22]([C:24]1[C:25]2[CH:34]=[CH:33][C:32]([O:35][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][C@@H:15]([O:18][CH3:19])[CH2:14]5)=[O:12])[S:10][C:3]=34)=[CH:31][C:26]=2[S:27][C:28]=1[CH2:29][CH3:30])=[O:23]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207677657-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 207677932-Ethyl-6-hydroxybenzo[b]thiophene-3-carboxylic acid methylamide

Product 1

HCID 586327992-Ethyl-6-[(2-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridin-7-yl)oxy]benzo[b]thiophene-3-carboxylic acid methylamideYield 27.4%

Procedure

This material was prepared by reacting 7-chloro-2-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}thieno[3,2-b]pyridine 4b (74 mg, 0.25 mmole) with 2-ethyl-6-hydroxybenzo[b]thiophene-3-carboxylic acid methylamide 134d (71 mg, 0.30 mmole) and Cs2CO3 (244 mg, 0.75 mmole) in a manner analogous to that described for example 1 to give a yellow solid (34 mg, 19%). 1H NMR (DMSO-d6, 300 MHz), δ8.59 (1H, d, J=5.31 Hz), 8.33 (1H, q, J=4.46 Hz), 8.06 (1H, s), 7.99 (1H, d, J=2.27 Hz), 7.81 (1H, d, J=8.84 Hz), 7.34 (1H, dd, J=2.27, 8.84 Hz), 6.76 (1H, d, J=5.56 Hz), 4.08-3.83 (3H, m), 3.67-3.48 (2H, m), 3.27, 3.24 (3H, s), 3.00 (2H, t, J=7.49 Hz), 2.83 (3H, d, J=4.55 Hz), 2.16-1.95 (2H, m), 1.28 (3H, t, J=7.58 Hz).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-053095096c124849a81ef6b5e64fd2fa
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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