Sodium Hydroxide → HCID 86692498, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (3 g) in Reference Example 123 (2), methylboronic acid (807 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (185 mg), palladium acetate (101 mg) and tripotassium phosphate (5.72 g) in 1,4-dioxane (20 ml) was stirred at 120° C. After completion of the reaction, the mixture was allowed to cool to room temperature, 4 N aqueous solution of sodium hydroxide (30 ml), water (30 ml), tetrahydrofuran (10 ml) and methanol (20 ml) were added thereto, and stirred at room temperature overnight. The organic solvent was evaporated in vacuo, then water and diethyl ether were added thereto, and the aqueous layer was separated. To the aqueous layer was added concentrated hydrochloric acid under ice-cooling to adjust the layer to pH 5, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (chloroform/methanol) to give the titled compound (697 mg) as a brown solid. MS (ESI) m/z: 286 (M+H)+.

Provenance & Evidence