Triethylamine → 3-Chloro-5-(3,4-difluorophenylethynyl)-pyridine

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1,2-Difluoro-4-iodobenzene	HCID 2724444	—
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-(3,4-difluorophenylethynyl)-pyridine	HCID 67047747	88%

Reaction Conditions

Temperature	60 °C

Reaction Steps

Add bis(triphenylphosphine)palladium (II) dichloride (49 mg, 0.07 mmol), copper (I) iodide (28 mg, 0.15 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (200 mg, 1.5 mmol) to a solution of 1,2-difluoro-4-iodobenzene (420 mg, 1.7 mmol) in triethylamine (3.1 mL, 22 mmol) and heat at 60° C. for 16 h. Cool to room temperature and concentrate. Purify the residue by silica gel chromatography, eluting with a gradient of 50:50 to 100:0 dichloromethane:hexanes, followed by a second silica gel chromatography, eluting with 95:5 to 85:15 hexanes:ethyl acetate to give the title compound as a white solid (320 mg, 88%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915424B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-f6090631ab784926a8b054afdce6dcfd
Source note	uspto-grants-2011_03