1,2-Dimethoxyethane → ethyl 1-[(4-phenyl-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, a mixture of the compound (400 mg, 1.02 mmol) obtained in Example 27a, [(E)-2-phenylethenyl]boronic acid (200 mg, 1.33 mmol), tetrakistriphenylphosphinepalladium (118 mg, 0.10 mmol), potassium carbonate (282 mg, 2.04 mmol), dimethoxyethane (5 mL) and water (1 mL) was stirred under microwave conditions at 150° C. for 10 min. The mixture was allowed to cool to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give a compound (49 mg, 12%) shown in Example 27b as a pale-yellow oil and a compound (85 mg, 27%) shown in Example 27c as a pale-red oil.

Provenance & Evidence