Sulfuric Acid → 3-(3-Trifluoromethylphenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid

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Reaction Conditions

Reaction Steps

A degassed mixture of 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid (20.0 mg, 68.5 μmol), 3-(trifluoromethyl)phenylboronic acid (19.5 mg, 0.103 mmol), and bis(triphenylphosphine)palladium(II) dichloride (2.4 mg, 3.4 μmol) in acetonitrile (0.3 mL) and 2N aqueous sodium carbonate solution (0.3 mL) was heated under microwave irradiation at 140° C. for 10 minutes. The cooled reaction mixture was acidified with 10% aqueous sulfuric acid. The solid was removed by filtration and the resultant filtrate was purified by preparative HPLC (5-45% MeCN over 45 min, 35 mL/min) to afford the title compound. 1H NMR (DMSO-D6, 400 MHz): 12.75 (s, 1H), 9.38-9.00 (m, 3H), 8.21 (m, 1H), 7.78 (m, 2H), 7.65-7.60 (m, 2H). LCMS (Method D): RT=10.76 min, M+H+=358.

Provenance & Evidence