2-Chloro-4-fluoropyridine → Tert-butyl 4-[3-(4-fluoropyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	2-Chloro-4-fluoropyridine	HCID 2782792	—
Reactant	2-(4-(3-(3,5-Difluoro-4-methoxyphenyl)prop-2-yn-1-ylidene)piperidin-1-yl)-3-nitropyridine	HCID 86627339	—
Reactant	tert-Butyl 4-(prop-2-yn-1-ylidene)piperidine-1-carboxylate	HCID 86661548	—
Product	Tert-butyl 4-[3-(4-fluoropyridin-2-yl)prop-2-ynylidene]piperidine-1-carboxylate	HCID 91261370	38.5%

Reaction Steps

The title compound was prepared following the procedure described for the Compound of Example 199, but using Compound 2b instead of Compound 1c and 2-chloro-4-fluoropyridine instead of 4-bromo-2,6-difluoroanisole. After the usual work-up procedure, purification was carried out by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc gradient from 95:5 to 60:40. Yield: 38.5%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08518916B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-1b7572d6b1e64c24aef166b5893311d3
Source note	uspto-grants-2013_08