Sodium Carbonate → HCID 86692428, compound

Participants

Reaction Conditions

Reaction Steps

Tetrahydrofuran (75 ml) was added to 1-(5-bromo-2-chloropyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (3 g) described in Reference Example 29, vinylboronic acid pinacol ester (2.01 g), tetrakis(triphenylphosphine)palladium (504 mg) and 2M aqueous solution of sodium carbonate (15.2 ml) and stirred at 90° C. for 4 hours. The reaction solution was cooled to 0° C., and a saturated aqueous solution of ammonium chloride and ethyl acetate were added therein. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified with column chromatography (n-hexane/ethyl acetate) to give 1-(2-chloro-5-vinylpyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.84 g).

Provenance & Evidence