Potassium Carbonate → Methyl 6-chloro-2-(3-fluorophenethylamino)nicotinate

https://huagongshe.com/reaction/2080272

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	N-methyl-2-pyrrolidone	HCID 13387	—
Reactant	2-(3-Fluorophenyl)ethanamine	HCID 533928	—
Reactant	Methyl 2,6-dichloropyridine-3-carboxylate	HCID 11106516	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Methyl 6-chloro-2-(3-fluorophenethylamino)nicotinate	HCID 57542459	54.8%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of methyl 2,6-dichloronicotinate (53.3 g, 0.26 mol), 3-fluorophenethyl amine (37.3 mL, 0.29 mol), K2CO3 (72 g 0.52 mol) and NMP (150 mL) was stirred at 100° C. for 10 hrs. The mixture was diluted with ethyl acetate (2×300 mL) and washed with brine. The organic layers were combined, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography using hexane-EtOAc (9:1) as eluant to give methyl 6-chloro-2-(3-fluorophenethylamino)nicotinate as an off-white solid (44 g, 54%). LRMS (M+H+) m/z 309.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07932270B2
Source dataset	uspto-grants-2011_04
ORD ID	ord-3854c1a5424541b1b5272a2417167bb6
Source note	uspto-grants-2011_04