Potassium Acetate → 5-Methoxy-2-(3-methyl-1,2,4-thiadiazol-5-yl)-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

In a microwave vial are combined 2-formyl-4-methoxyphenylboronic acid (432 mg, 2.40 mmol), 5-chloro-3-methyl-1,2,4-thiadiazole (270 mg, 2.00 mmol), potassium acetate (390 mg, 4.00 mmol), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)-dichloropalladium(II) (283 mg, 0.40 mmol) in 1,4-dioxane (6 mL) and water (0.50 mL). The reaction vial is sealed and stirred at 100° C. for 20 hours. The reaction mixture is cooled to ambient temperature and poured into water and extracted with EtOAc (3×). The combined organics are dried (MgSO4), filtered and concentrated. Purification via flash chromatography (12 g silica gel, 5-40% EtOAc/heptane) affords 5-methoxy-2-(3-methyl-1,2,4-thiadiazol-5-yl)-benzaldehyde which is used without further purification.

Provenance & Evidence