Cesium carbonate → 2-Methyl-6(2-[pyrrolidin-1-ylmethyl]thieno[3,2-b]pyridin-7-yloxy)benzo[b]thiophene-3-carboxylic acid methylamide

HRID 985318Notes

Reaction equation

HRID 985318 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([CH2:11][N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[S:10][C:3]=12.[CH3:17][NH:18][C:19]([C:21]1[C:22]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][C:23]=2[S:24][C:25]=1[CH3:26])=[O:20].C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:17][NH:18][C:19]([C:21]1[C:22]2[CH:30]=[CH:29][C:28]([O:31][C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[C:9]([CH2:11][N:12]5[CH2:16][CH2:15][CH2:14][CH2:13]5)[S:10][C:3]=34)=[CH:27][C:23]=2[S:24][C:25]=1[CH3:26])=[O:20]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 207678636-Hydroxy-n,2-dimethyl-1-benzothiophene-3-carboxamideHCID 221435927-Chloro-2-(pyrrolidin-1-ylmethyl)thieno[3,2-b]pyridine

Product 1

HCID 207678922-Methyl-6(2-[pyrrolidin-1-ylmethyl]thieno[3,2-b]pyridin-7-yloxy)benzo[b]thiophene-3-carboxylic acid methylamide

Procedure

This material was prepared from 7-Chloro-2-(pyrrolidin-1-ylmethyl)thieno[3,2-b]pyridine 115a, 6-hydroxy-2-methyl-benzo[b]thiophene-3-carboxylic acid methylamide 1d and cesium carbonate in a similar manner as described in example 1. 1H-NMR (DMSO-d6, 400 MHz) 68.44 (1H, d, J=5.3 Hz), 8.27 (1H, q, J=4.6 Hz), 7.91 (1H, d, J=2.3 Hz), 7.83 (1H, d, J=8.6 Hz), 7.43 (1H, s), 7.28 (1H, dd, J=2.3, 8.6 Hz), 6.60 (1H, d, J=5.6 Hz), 3.93 (2H, s), 2.82 (3H, d, J=4.8 Hz), 2.60 (3H, s), 2.54 (4H, bs), 1.72 (4H, s); MS m/z 438 (M+H)+;

Sources & evidence

ORD record
ord-93cd8ef7d86747608c683d72b81f9adb
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

Loading…