Nitrogen → 6-(2-ethylbutyl)-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One	HCID 73712352	—
Reactant	HCID 178444614	HCID 178444614	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	6-(2-ethylbutyl)-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One	HCID 73712330	23%

Reaction Conditions

Temperature	160 °C

Reaction Steps

Into a dry microwave vial under N2 was added 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(dppf)Cl2 (about 5 mol %), and CuI (about 6 mol %) in dry THF (0.5 mL) followed by 2-ethylbutyl zinc bromide (0.273 mL, 0.138 mmol (0.5M in THF)) dropwise. The solution was heated in the microwave for 10 minutes at 160° C., filtered, and was purified by Prep HPLC to give 4.7 mg (18%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 445 (M+H)+; 1H NMR (300 MHz, MeOH) δ ppm 0.90 (t, 6H), 1.29-1.38 (m, 4H), 1.60 m, 1H), 1.99 (m, 2H), 2.39 (br d, 2H), 2.60 (m, 2H), 3.24 (br t, 2H), 3.72 (br d, 2H), 3.97 (m, 3H), 5.42 (s, 1H), 6.31-6.40 (m, 1H), 6.95 (d, 1H), 7.24-7.54 (m. 8H), 7.84 (d, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06921821B2
Source dataset	uspto-grants-2005_07
ORD ID	ord-4eb11f8e6cdb4ea9961f5aa26870f1cc
Source note	uspto-grants-2005_07