Triethylamine → 3-Chloro-5-(3-chloro-4-fluorophenylethynyl)-pyridine

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Chloro-1-fluoro-4-iodobenzene	HCID 2724605	—
Reactant	3-Chloro-5-ethynylpyridine	HCID 23500887	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178419050	HCID 178419050	—
Product	3-Chloro-5-(3-chloro-4-fluorophenylethynyl)-pyridine	HCID 67047727	71%

Reaction Conditions

Temperature	60 °C

Reaction Steps

Add bis(triphenylphosphine)palladium (II) dichloride (64 mg, 0.091 mmol), copper (I) iodide (35 mg, 0.18 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (250 mg, 1.8 mmol) to a solution of 2-chloro-1-fluoro -4-iodobenzene (560 mg, 2.2 mmol) in triethylamine (3.8 mL, 27 mmol) and heat at 60° C. for 5 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 50:50 to 100:0 dichloromethane:hexanes, followed by a second silica gel chromatography, eluting with 100:0 to 90:10 hexanes:ethyl acetate, to give the title compound as a white solid (340 mg, 70%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915424B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-29627e92ed6e4a8c893f2e1b5633662b
Source note	uspto-grants-2011_03