Triethylamine → 3-Bromo-5-(3-chlorophenylethynyl)-pyridine

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3,5-Dibromopyridine	HCID 69369	—
Reactant	1-Chloro-3-ethynylbenzene	HCID 123086	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178419050	HCID 178419050	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	3-Bromo-5-(3-chlorophenylethynyl)-pyridine	HCID 67047593	46.2%

Reaction Conditions

Temperature	50 °C

Reaction Steps

Add triethylamine (2.38 mL, 16.88 mmol), copper (I) iodide (80.4 mg, 0.422 mmol) and bis(triphenylphosphine)palladium (II) dichloride (148 mg, 0.211 mmol) to a solution of 3,5-dibromopyridine (1 g, 4.22 mmol) and 1-chloro-3-ethynylbenzene, (prepared as described in PREPARATION 12), (574 mg, 4.22 mmol) in ethyl acetate (4.22 mL). Stir under nitrogen at 50° C. for 18 h. Concentrate and purify the residue by silica gel chromatography, eluting with 100:0 to 0:100 hexanes:ethyl acetate, to give the title compound (571 mg, 46%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915424B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-a5ea1f42ceb44f978be9fd8bb0227719
Source note	uspto-grants-2011_03