Sodium Bicarbonate → 2-[(Aminocarbonyl)amino]-5-[4-formylphenyl]thiophene-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-bromo-2-(carbamoylamino)thiophene-3-carboxamide (1.0 g, 3.79 mmol), 4-formylphenylboronic acid (0.625 g, 4.17 mmol) and tetrakis(triphenylphosphine) Pd catalyst (0.438 g, 0.379 mmol) in DME (50 ml) was added a saturated aqueous solution of sodium hydrogen carbonate (10 ml). The reaction vessel was flushed with nitrogen and heated to 90° C. overnight. LCMS indicated complete consumption of the starting material. The reaction mixture was concentrated using a rotary evaporator. The resultant dark brown residue was dissolved in DCM (17 ml) and stirred with aqueous 2M sodium hydroxide solution (8.5 ml) for 20 minutes. Diethyl ether (20 ml) was added and the mixture stirred for a further 30 minutes. The resultant suspension was sonicated for 2 minutes. Filtration gave a precipitate, which was washed with hot diethyl ether to give a coloured solid (440 mg).

Provenance & Evidence