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

HRID 985336Notes

Reaction equation

HRID 985336 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[OH:11][C:12]1[CH:13]=[CH:14][C:15]2[C:19]([C:20]([O-:22])=[O:21])=[C:18]([CH3:23])[S:17][C:16]=2[CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:23][C:18]1[S:17][C:16]2[CH:24]=[C:12]([O:11][C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[CH:9][S:10][C:3]=34)[CH:13]=[CH:14][C:15]=2[C:19]=1[C:20]([OH:22])=[O:21]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 112752517-Chlorothieno[3,2-b]pyridineHCID 178435028HCID 178435028, compound

Product 1

HCID 221435062-Methyl-6-(thieno[3,2-b]pyridin-7-yloxy)benzo[b]thiophene-3-carboxylic acidYield 27.2%

Procedure

This material was prepared by reacting 7-chlorothieno[3,2-b]pyridine (170 mg, 1.0 mmole) with methyl 6-hydroxy-2-methylbenzo[b]thiophene-3-carboxylate 11a (267 mg, 1.2 mmole) and Cs2CO3 (488 mg, 1.5 mmole) in a manner similar to that previously described for example 1. Silica gel chromatography (10% MeOH/CHCl2) provided the title compound as a brown viscous oil (93 mg, 27%) of. 1H NMR (DMSO-d6, 300 MHz) δ8.47 (1H, d, J=5.27 Hz), 8.41 (1H, d, J=8.85 Hz), 8.11 (1H, d, J=5.46 Hz), 7.93 (1H, d, J=2.07 Hz), 7.55 (1H, d, J=7.55 Hz), 7.32 (1H, dd, J=2.26, 8.85 Hz), 6.64 (1H, d, J=5.27 Hz), 2.77 (3H, s).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-c6f49fd32447428dbe6040bbc8b74198
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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