Potassium Carbonate → 5-(6-chloro-5-formylpyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2,6-Dichloropyridine-3-carbaldehyde	HCID 12259383	—
Reactant	2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide	HCID 68239402	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-(6-chloro-5-formylpyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide	HCID 90332470	86.3%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a degassed solution of 2,6-dichloronicotinaldehyde (315 mg, 1.79 mmol) and 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (600 mg, 1.19 mmol) in 1,4-dioxane (8 mL) and water (300 μL) was added K2CO3 (330 mg, 2.40 mmol) and Pd(dppf)Cl2 (175 mg, 0.24 mmol) under N2 protection. The resulting mixture was heated to 80° C. and stirred at this temperature overnight. The reaction was cooled, filtered through a pad of celite and washed with ethyl acetate. The combined filtrate was evaporated in vacuo. The resulting residue was purified using column chromatography (eluted with 0-30% EtOAc/DCM) to provide 5-(6-chloro-5-formylpyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (530 mg, yield: 86%) MS (M+H)+: 516.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09243002B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-16b807a693854fa8a20c44a7a8574b44
Source note	uspto-grants-2016_01