Triphenylphosphine → 2-(5-Chloropyridin-2-yl)furo[3,2-c]pyridin-4(5H)-one

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	2-bromofuro[3,2-c]pyridin-4(5H)-one	HCID 74787775	—
Reactant	Lithium 1-(5-chloropyridin-2-yl)-4-methyl-2,6,7-trioxa-1-borabicyclo[2.2.2]octan-1-uide	HCID 131737090	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Dimethylacetamide	HCID 31374	—
Product	2-(5-Chloropyridin-2-yl)furo[3,2-c]pyridin-4(5H)-one	HCID 117949619	29.9%

Reaction Conditions

Temperature	250 °C

Reaction Steps

A mixture of 2-bromofuro[3,2-c]pyridin-4(5H)-one (200 mg), lithium 1-(5-chloropyridin-2-yl)-4-methyl-2,6,7-trioxa-1-borabicyclo[2.2.2]octan-1-uide (462 mg), palladium(II) acetate (21.0 mg), copper(I) iodide (178 mg), triphenylphosphine (49.0 mg) and DMA (1.0 mL) was heated at 250° C. for 30 min under microwave irradiation. The reaction mixture was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and the obtained solid was washed with diisopropyl ether to give the title compound (69.0 mg) as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09440987B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-a5b547294aa6426899d98b6f131425ae
Source note	uspto-grants-2016_09