1H-1,2,4-Triazole → HCID 59313851, compound

Participants

Role	Name	HCID	Charge
Reactant	1H-1,2,4-Triazole	HCID 9257	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-(3-bromo-5-nitrophenoxy)-N,N-dimethylethanamine	HCID 59313993	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	HCID 59313851	HCID 59313851	57%

Reaction Steps

Intermediate 16A (200 mg, 0.69 mmol), copper(I) iodide (65.9 mg, 0.35 mmol), potassium carbonate (287 mg, 2.1 mmol) and 1H-1,2,4-triazole (143 mg, 2.075 mmol) in NMP (2 mL) were heated at 120° C. for 6 hours. The reaction mixture was diluted with dichloromethane, and filtered through a plug of silica gel and washed with ethyl acetate. The filtrate was concentrated, and the residue was purified by reverse phase HPLC to obtain Intermediate 16B (109 mg, 56.8% yield) as a yellow solid. HPLC: Rt=0.74 min. (PHENOMENEX® Luna 5 micron C18 4.6×30 mm, 10-90% aqueous methanol containing 0.1% TFA, 2 min. gradient, flow rate=5 mL/min, detection at 254 nm). MS (ES): m/z=278.08 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08252795B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-9cd1b105d2e44f558f20b82ae5ba426f
Source note	uspto-grants-2012_08