2-Chloro-5-(trifluoromethyl)pyridine → HCID 90159268, compound

https://huagongshe.com/reaction/2200082

Participants

Role	Name	HCID	Charge
Reactant	2-Chloro-5-(trifluoromethyl)pyridine	HCID 92342	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	tert-butyl N-(morpholin-2-ylmethyl)carbamate	HCID 19081107	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	Toluene	HCID 1140	—
Product	HCID 90159268	HCID 90159268	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

tert-Butyl morpholin-2-ylmethylcarbamate (1.0 g, 4.62 mmol), 2-chloro-5-(trifluoromethyl)pyridine (839 mg, 4.62 mmol), Pd(dba)2 (133 mg, 0.23 mmol), sodium tert-butoxide (533 mg, 5.55 mmol) and X-Phos (220 mg, 0.46 mmol) were combined in toluene (10 mL). The mixture was degassed with nitrogen for 5 minutes and sealed. The resulting mixture was stirred at 100° C. for 12 h. The mixture was filtered and rinsed with THF. Solvents were evaporated and the residue was purified by ISCO flash column chromatography (0% to 35% ethyl acetate in hexanes) to give the desired compound as a light brown waxy material (350 mg, 21%). [MH]+=362.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09359337B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-53eb9396cf7b4363b3a6b10b9aa094bf
Source note	uspto-grants-2016_06