Potassium Carbonate → Cis(+/-)1-{2-[4-azido-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	5,7-Difluoro-1,2-dihydroquinolin-2-one	HCID 64208249	—
Reactant	tert-butyl{1-[2-(7,8-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate	HCID 86642603	—
Reactant	Cis(+/-)2-(4-azido-3-hydroxypiperidin-1-yl)ethyl methanesulfonate	HCID 86642609	—
Product	Cis(+/-)1-{2-[4-azido-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one	HCID 86642608	—

Reaction Steps

5,7-Difluoroquinolin-2(1H)-one (Intermediate 25) (389 mg, 2.15 mmol) was deprotonated with sodium hydride (95 mg, 60% in oil, 2.36 mmol) and alkylated with cis(±) 2-(4-azido-3-hydroxypiperidin-1-yl)ethyl methanesulfonate (Intermediate 44) (2.15 mmol) as described for Intermediate 20, except after 24 hours, potassium carbonate (100 mg, 0.72 mmol) was added and the resulting mixture was stirred for another 24 hours at room temperature to give the product as a colorless hard foam, 195 mg (26%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07875715B2
Source dataset	uspto-grants-2011_01
ORD ID	ord-4be2bbcb67ff4e3193b48c3b4ba07c68
Source note	uspto-grants-2011_01