1,2-Dichloroethane → HCID 71522361, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-fluoro-2-{[(3S,6R)-6-methylpiperidin-3-yl]ethynyl}pyridine (193 mg, 0.884 mmol), EDC (339 mg, 1.77 mmol), HOAT (241 mg, 1.77 mmol), and 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (216 mg, 1.06 mmol) in DMF (6 mL) was treated with triethylamine (0.37 mL, 2.7 mmol) and the reaction stirred at 50° C. for 2 d. The reaction was diluted with sat'd, aqu. NaHCO3 and extracted twice with EtOAc. The organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel flash chromatography eluting with 0-65% EtOAc in hexanes to provide the pure title compound as an off-white foam. The pure material gave a high resolution mass spectrum (ES+) m/z of 404.1883, calculated for M+H+ [C23H22FN5O: 404.1881] and a proton NMR spectra consistent with theory.

Provenance & Evidence