Sodium Carbonate → HCID 22350273, compound

Participants

Reaction Conditions

Reaction Steps

Tetrakis(triphenylphosphine)palladium (0) (0.58 g, 0.5 mmol), and a degassed solution of 2.0M Na2CO3 (10 mL) are added to a degassed solution of ethyl 2-bromo-1,3-thiazole-5-carboxylate (1.18 g, 5.0 mmol) and 2-fluorophenylboronic acid (0.77 g, 5.5 mmol) in DME (10 mL). The resulting suspension is stirred under argon at 80° C. for 4 hr. The reaction mixture is cooled, diluted with EtOAc, and then washed with two portions of 1.0 M NaOH, then one portion of brine. The combined organic phases are concentrated in vacuo, and the resulting oil purified with flash chromatography to give ethyl 2-(2-fluorophenyl)-1,3-thiazole-5-carboxylate. Yield 37%. HRMS (FAB) calculated for C12H10FNO2S+H 252.0495, found 252.0496.

Provenance & Evidence