Potassium Carbonate → 5-(6-chloro-5-(1-(hydroxymethyl)cyclopropyl)pyridin-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-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)boronic acid	HCID 90332474	—
Reactant	(1-(6-Bromo-2-chloropyridin-3-yl)cyclopropyl)methanol	HCID 90332508	—
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-(1-(hydroxymethyl)cyclopropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide	HCID 90332478	37.6%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a solution of (1-(6-bromo-2-chloropyridin-3-yl)cyclopropyl)methanol (100 mg, 0.381 mmol) and (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)boronic acid (160 mg, 0.381 mmol) in 1,4-Dioxane (2 mL) and water (20 μL) was added K2CO3 (105 mg, 0.762 mmol) and Pd(dppf)Cl2 (55 mg, 0.075 mmol). The mixture was heated to 70° C. and stirred overnight. Filtration through a pad of celite removed the solid. After washing with ethyl acetate, the combined filtrate was concentrated in vacuo. Preparative TLC gave 5-(6-chloro-5-(1-(hydroxymethyl)cyclopropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (80 mg, yield: 37.6%) MS (M+H)+: 559.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09243002B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-cc863e542c5e45ef9ba1232402728801
Source note	uspto-grants-2016_01