Sodium Carbonate → HCID 86680380, compound

Participants

Reaction Steps

Under argon atmosphere, to 2-[3-chloro-5-((R)-2,2,2-trifluoro-1-methylethoxymethyl)phenyl]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (269 mg) were sequentially added a solution of 5-iodo-1-phenyl-1H-pyrazol-3-ylamine (181 mg) prepared according to the same procedures as Preparation 2 in 1,2-dimethoxyethane (2.0 ml), a 2M aqueous solution of sodium carbonate (1.0 ml), tricyclohexylphosphine (36 mg) and palladium (II) acetate (15 mg) at room temperature, and the mixture was stirred at 100° C. for 2 hours. This reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate were added thereto, the mixture was filtered through Celite, and subjected to elution with ethyl acetate. The filtrate was extracted with ethyl acetate. The resulting organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (eluent: n-hexane/ethyl acetate=3/7) to give the titled compound (196 mg).

Provenance & Evidence