Cesium carbonate → Toluene-4-sulfonic acid 2-methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-phenyl ester

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-(4-Methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one	HCID 57649511	—
Reactant	4-Bromo-2-methoxyphenyl 4-methylbenzene-1-sulfonate	HCID 86629205	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Toluene-4-sulfonic acid 2-methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-phenyl ester	HCID 57649518	86%

Reaction Steps

Combine 2-(4-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (0.245 g, 0.943 mmol), toluene-4-sulfonic acid 4-bromo-2-methoxy-phenyl ester (0.404 g, 1.13 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (27.3 mg, 0.05 mmol), and Cs2CO3 (0.461 g, 1.41 mmol) in dioxane (25 mL). Purge the reaction vessel with nitrogen for 5 min, and then add Pd2(dba)3 (8.6 mg, 0.09 mmol). Reflux the reaction mixture and stir 16 h. Dilute with EtOAc (100 mL), wash with water (2×30 mL), dry with Na2SO4, filter and concentrate. Purify the crude material by chromatography, eluting with 30-50% EtOAc/hexanes to give 0.432 g (86%) of the title compound. LC-MS/ES m/z 536.0 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08263772B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-f0e50bf4497d4795b82413b4739b8bf4
Source note	uspto-grants-2012_09