2-Aminothiazole → HCID 10357612, compound

Participants

Reaction Conditions

Reaction Steps

A solution of triphenylphosphine (771 mg, 2.94 mmol) in methylene chloride (7 mL) cooled to 0° C. was treated with N-bromosuccinimide (523 mg, 2.94 mmol). The reaction was stirred at 0° C. for 15 min. At this time, the reaction was treated with 6-fluoro-1-isopropyl-1H-indole-3-carboxylic acid (500 mg, 2.26 mmol). The reaction was stirred at 0° C. for 15 min and then was allowed to warm to 25° C. where it was stirred for 15 min. The reaction was then treated with 2-aminothiazole (521 mg, 5.20 mmol) and stirred at 25° C. for 18 h. At this time, the mixture was partitioned between water (75 mL) and ethyl acetate (75 mL) and treated with a 1N aqueous hydrochloric acid solution (50 mL). The organic layer was then washed with a saturated aqueous sodium bicarbonate solution (1×50 mL), water (1×50 mL), and a saturated aqueous sodium chloride solution (1×50 mL). The organic layer was then dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 1/1 hexanes/ethyl acetate) afforded 6-fluoro-1-isopropyl-1H-indole-3-carboxylic acid thiazol-2-ylamide (160 mg, 23%) as pink solid: mp 203-204° C.; EI-HRMS m/e calcd for C15H14FN3OS (M+) 303.0842, found 303.0844.

Provenance & Evidence