Phenylboronic Acid → 2-[2-(Diphenylmethylidene)hydrazino]-4-methoxypyridine

Participants

Reaction Steps

500 mg (3.48 mmol) 2-chloro-4-methoxypyridine, 752 mg (3.83 mmol) benzophenone hydrazone, 469 mg (4.88 mmol) sodium tert-butylate, 15.6 mg (0.07 mmol) palladium(II) acetate, 21.2 mg (0.17 mmol) phenylboronic acid and 43.4 mg (0.07 mmol) racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl are heated in degassed toluene at 90° C. overnight under argon. After cooling, the reaction mixture is poured into water, the aqueous phase is extracted several times with ethyl acetate and the combined organic phases are dried over sodium sulfate, filtered and concentrated. The residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient).

Provenance & Evidence