Tributylphosphine → HCID 121386221, compound

https://huagongshe.com/reaction/2203003

Participants

Role	Name	HCID	Charge
Reactant	Tributylphosphine	HCID 13831	—
Reactant	1,1'-(Azodicarbonyl)dipiperidine	HCID 73042	—
Reactant	(5-Bromothiophen-3-yl)methanol	HCID 19006171	—
Reactant	1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one	HCID 89690281	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 121386221	HCID 121386221	26.9%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (87 mg), (5-bromo-3-thienyl)methanol (119 mg) and tributylphosphine (188 mg) in THF (4 ml) was added 1,1′-(azodicarbonyl)dipiperidine (234 mg), and the reaction mixture was stirred at 60° C. for 3 h. The reaction mixture was then cooled to room temperature, concentrated, and purified by silica gel column chromatography (hexane/EtOAc then MeOH/EtOAc). The resulting solid was recrystallized from EtOH/hexane to give the title compound (38 mg) as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09365540B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-c5595bf1044f4147a228359b132a80f1
Source note	uspto-grants-2016_06