Sodium Carbonate → Methyl 4-(((benzyloxy)carbonyl)amino)-5-bromo-2-(4-chlorophenyl)thiophene-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Palladium tetrakis-triphenylphosphine (19.3 mg, 17 μmol) was added to a degassed solution of dibromide 4 (150 mg, 334 μmol) and 4-chlorophenylboronic acid 5 (54.8 mg, 350 μmol) in ethanol: water:toluene (2:1:1, 1.67 mL) and sodium carbonate (177 mg, 1.6 mmol). The resulting mixture was heated under N2 and stirred for 1 h at 80° C. The mixture was then cooled filtered through a 0.45 μm syringe filter and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 6 (76.8 mg, 48%) as a solid: LRESIMS m/z 479.8 [M+H]+, calcd. for C20H16Br1Cl1N1O4S1 480.0.

Provenance & Evidence