Potassium Carbonate → (E)-2-(3-fluorophenethylamino)-6-(prop-1-enyl)-N-(pyridin-3-ylmethyl)nicotinamide

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	((1E)-prop-1-en-1-yl)boronic acid	HCID 6157276	—
Reactant	chloride 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide	HCID 86620472	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(E)-2-(3-fluorophenethylamino)-6-(prop-1-enyl)-N-(pyridin-3-ylmethyl)nicotinamide	HCID 59738250	86%

Reaction Conditions

Temperature	125 °C

Reaction Steps

A mixture of chloride 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide (100 mg, 0.260 mmol), trans-1-propen-1-yl boronic acid (27 mg, 0.312 mmol), PdCl2(dppf)2 (14 mg, 0.026 mmol), 2N K2CO3(0.39 mL, 0.78 mmol) and THF (1.5 mL) was stirred at 125° C. for 30 min. The mixture was filtered through the silica gel pad and washed with EtOAc. The filtrate was concentrated to dryness and purified on RP-HPLC using a mixture of acetonitrile and H2O to give (E)-2-(3-fluorophenethylamino)-6-(prop-1-enyl)-N-(pyridin-3-ylmethyl)nicotinamide as a pale yellow solid (59 mg, 86%). LRMS (M+H+) m/z 391.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07939548B2
Source dataset	uspto-grants-2011_05
ORD ID	ord-1fd1104ffdf440eebb2b026c19def4aa
Source note	uspto-grants-2011_05