Sodium Carbonate → HCID 91206831, compound

Participants

Reaction Steps

To a solution of tert-butyl{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}carbamate (1.30 g, 3.16 mmol) in pyridine (20 mL) was added cyclopropanecarbonyl chloride (345 μL, 3.80 mmol), and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added aqueous sodium hydrogen carbonate solution (30 mL), and the mixture was extracted with ethyl acetate (50 mL×3). The organic layer was washed successively with water (50 mL) and saturated brine (30 mL), and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in a mixed solvent of methanol (10 mL)/tetrahydrofuran (10 mL), sodium carbonate (335 mg, 3.16 mmol) was added, and the mixture was stirred at room temperature for 17 hr. To the reaction mixture was added aqueous ammonium chloride solution (30 mL), and the mixture was extracted with ethyl acetate (50 mL×3). The organic layer was washed with saturated brine (20 mL), and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5→50/50) to give the title compound (1.22 g, 81%) as a white powder.

Provenance & Evidence