Dimethyl Sulfoxide → 3-Chloroisoquinoline-6-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-bromo-3-chloroisoquinoline (93.5 mg, 0.386 mmol), 2-(trimethylsilyl)-ethanol (456 mg, 3.856 mmol), Pd(OAc)2 (8.7 mg, 0.039 mmol), 1,1′-Bis(diphenyl-phosphino)ferrocene (45.1 mg, 0.077 mmol) and DMSO (27 uL, 0.386 mmol) in DMF (6 mL) was placed in a microwave tube (15 mL). The reaction was saturated with CO gas for 10 minutes before the tube was sealed and stirred at 120° C. under microwave irradiation for 10 hours. The reaction mixture was diluted with EtOAc and filtered. 2M NaOH (0.5 mL) was added to the filtrate and extracted with brine. The combined aqueous layers were washed with EtOAc and acidified carefully with drops of concentrated HCl to pH=3. The resulting cloudy solution was extracted with EtOAc, dried over sodium sulphate and concentrated in vacuo to afford the title compound as light brown solid (21 mg, 26%).

Provenance & Evidence