Phenylboronic Acid → HCID 86659953, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3.3 g (16.41 mmol) of 2-bromo-N,N-dimethylpyridin-4-amine in 40 mL of anhydrous toluene, 3.5 g (18.05 mmol) of benzophenone hydrazone, 2.2 g (23 mmol) of anhydrous sodium tert-butoxide and 100 mg (0.82 mmol) of benzeneboronic acid in 40 mL of toluene are added, under argon, at room temperature, after having degassed the reaction medium under argon, 74 mg (0.33 mmol) of palladium acetate and 205 mg (0.33 mmol) of racBINAP. The reaction medium is then heated for 4 hours at 80° C. The reaction medium is taken up in 200 mL of EtOAc, washed successively with water (3×30 mL), with saturated NaHCO3 solution (30 mL) and with brine (30 mL) and then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a DCM/MeOH gradient of from 0 to 10% MeOH. After concentrating under reduced pressure, 4.5 g of 2-[2-(diphenylmethylidene)hydrazino]-N,N-dimethylpyridin-4-amine are obtained in the form of a red solid.

Provenance & Evidence