Triethylamine → 2-Fluoro-5-(5-methoxypyridin-3-ylethynyl)-benzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3-Ethynyl-5-methoxypyridine	HCID 21097349	—
Reactant	2-Fluoro-5-iodobenzamide	HCID 67047811	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178419050	HCID 178419050	—
Product	2-Fluoro-5-(5-methoxypyridin-3-ylethynyl)-benzamide	HCID 67048341	88.8%

Reaction Conditions

Temperature	60 °C

Reaction Steps

Add bis(triphenylphosphine)palladium (II) dichloride (70 mg, 0.10 mmol), copper (I) iodide (38 mg, 0.20 mmol), and 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (350 mg, 2.6 mmol) to a solution of 2-fluoro-5-iodobenzamide, (prepared as described in PREPARATION 44), (0.54 g, 2.0 mmol) in triethylamine (3.1 mL, 30.3 mmol) and heat at 60° C. for 18 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 100:0 to 0:100 dichloromethane:ethyl acetate, to give the title compound as a white solid (480 mg, 68%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915424B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-c8e8b80d793b4bb1b4804ab11c1a8330
Source note	uspto-grants-2011_03