Sodium Carbonate → HCID 59656659, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-amino-5-bromo-benzo[b]thiophene-2-carboxylic acid amide (90 mg, 0.33 mmol) in DMF (5 mL) was added phenylboronic acid (1.2 eq., 50 mg) at room temperature, under nitrogen. The resulting mixture was degassed and placed under nitrogen after which time sodium carbonate (1.2 eq., 43 mg) and Pd(Ph3)4 (0.4 eq., 155 mg) were added. The reaction was degassed again and warmed to 80° C. overnight, under nitrogen. Upon cooling to room temperature, the reaction was concentrated to dryness and the remaining residue was purified via flash column chromatrography (5 g SiO2, 0-40% EtOAc/dichloromethane). The product-containing fractions were concentrated to give the product which was still contaminated. The brown solid was diluted with 1:1 CH3CN/H2O and the remaining solids were removed via filtration. The filtrate was re-purified using preparatory reverse phase HPLC to give 7.4 mg (8%) of the title compound as a white solid.

Provenance & Evidence