6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One → HCID 73712345, compound

Participants

Role	Name	HCID	Charge
Reactant	6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One	HCID 73712352	—
Reactant	HCID 178455869	HCID 178455869	—
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	HCID 73712345	HCID 73712345	73.4%

Reaction Conditions

Temperature	160 °C

Reaction Steps

Into a dry microwave vial under nitrogen 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 n-propyl 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 13.6 mg (57%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 403 (M+H)+; 1H NMR (300 MHz, MeOH) δ ppm 0.96 (t, 3H), 1.70 (m, 2H), 1.98-2.01 (m, 2H), 2.39 (br d, 2H), 2.69 (t, 2H), 3.23 (br t, 2H), 3.72 (m, 2H), 3.88-3.98 (m, 3H), 5.42 (s, 1H), 6.30-6.40 (m, 1H), 6.95 (d, 1H), 7.24-7.54 (m 0.8H), 7.85 (s, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06921821B2
Source dataset	uspto-grants-2005_07
ORD ID	ord-990d47ffb18b41ebb7cac08ada974b15
Source note	uspto-grants-2005_07