Hydrochloric Acid → (2-Aminophenyl)(5-fluoropyridin-2-yl)methanone

Participants

Reaction Conditions

Reaction Steps

2-Bromo-5-fluoropyridine (10 g, 56.8 mmol) and 2-aminobenzonitrile (5.6 g, 47.4 mmol) were dissolved in 100 mL of toluene and cooled to −30° C. To the resulting solution was added nBuLi (1.6 M in hexanes, 65 mL, 104 mmol, 2.2 equv) dropwise, and the reaction mixture was warmed to 0 deg for 90 minutes. The reaction mixture was then poured into 100 mL of cooled 3N HCl and stirred for 15 minutes, then 5N NaOH was added until the reaction mixture turned basic. The reaction mixture was extracted with CH2Cl2 (3×100 ml), washed with brine (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (0% to 30% EtOAc/hexanes) gave the title compound as a solid (LC/MS found: 217.2)

Provenance & Evidence