Water → methyl 2-(tert-butoxy)-2-[5-(3,4-dihydro-2H-1-benzopyran-6-yl)-2-methyl-1,3-thiazol-4-yl]acetate

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Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, sodium carbonate (22 mg, 0.21 mmol), water (1 mL), palladium tetrakis(triphenylphosphine) (32 mg, 0.03 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (55 mg, 0.21 mmol) were added to a solution of methyl 2-(5-bromo-2-methyl-1,3-thiazol-4-yl)-2-(tert-butoxy)acetate (15d) (70 mg, 0.21 mmol) in N,N-dimethylformamide (4 mL). The mixture was heated at 110° C. for 1 hour. The mixture was then cooled at room temperature, concentrated and water (20 mL) was added. The aqueous layer was extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (20 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 90/10) to afford the desired product as a white solid (48 mg, 0.13 mmol, 61%).

Provenance & Evidence