Potassium Carbonate → Phenylboronic Acid

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (0.166 g, 1.2 mmol) was added to a solution of 2-cyclopentyl-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (0.235 g, 1 mmol) and 3-(bromomethyl)phenylboronic acid (0.257 g, 1.2 mmol) in acetone (10 mL). After stirring for 1 h at 60° C., the reaction mixture was cooled to room temperature and filtered and the filtrate was evaporated under reduced pressure to give crude 34(2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)phenylboronic acid as a colorless solid (0.315 g, 85%). The crude product was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 2H), 7.83 (s, 1H), 7.73-7.68 (m, 2H), 7.56 (s, 1H), 7.47 (d, 1H, J=7.8 Hz), 7.32 (t, 1H, J=7.8 Hz), 7.04 (d, 1H, J=8.7 Hz), 5.25 (s, 2H), 4.85-4.81 (m, 1H), 2.01-1.98 (m, 2H), 1.75-1.59 (m, 6H). LC-MS (ESI) Calcd for C19H20BNO4S [M+H]+: 370.12. Found: 369.90.

Provenance & Evidence