Triethylamine → HCID 67047760, compound

Participants

Reaction Steps

Add bis(triphenylphosphine)palladium (II) dichloride (46 mg, 0.07 mmol), copper (I) iodide (25 mg, 0.13 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (200 mg, 1.45 μmmol) to a solution of 2-fluoro-5-iodo-N,N-dimethylbenzamide, (prepared as described in PREPARATION 45), (0.600 g, 2.1 mmol) in triethylamine (4.3 mL, 31 mmol) and place in an oil bath at 70° C. Add toluene (10 mL) and heat for 2 h. Concentrate and purify by silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes, to give the free base of the title compound as a colorless oil. Dissolve the free base in diethyl ether (50 mL) and add 2 M hydrogen chloride in diethyl ether (2.6 mL, 5.2 mmol). Stir for 10 min, concentrate, triturate with diethyl ether and dry to give the title compound as a light yellow solid (350 mg, >99%).

Provenance & Evidence