Sodium Carbonate → HCID 86656712, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl 4-bromo-6-methylbenzo[d]thiazol-2-ylcarbamate (0.6 g, 1.75 mmol), 3-chloro-4-fluorophenylboronic acid (0.5 g, 2.62 mmol), palladium(II) acetate (0.08 g, 0.35 mmol), triphenylphosphine (0.3 g, 1.05 mmol) was added degassed dioxane (10 mL) and degassed 1 M aqueous sodium carbonate (5.24 mL, 5.24 mmol). The mixture was heated to 100° C. for 16 hours under argon and then diluted with ethyl acetate, washed with water, brine and concentrated. The residue was redissolved in trifluoroacetic acid (2 mL) and stirred for 15 minutes. The solvent was evaporated, the residue redissolved in dichloromethane, washed with saturated sodium hydrogen carbonate, dried with sodium sulfate and concentrated. The product was purified by column chromatography on silica gel using n-heptane:ethyl acetate (v/v=9:1-4:1) as eluent to yield the title compound as white solid (0.4 g, 80%).

Provenance & Evidence