Sodium Carbonate → HCID 24831457, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Example 3 (0.16 g, 0.50 mmol) and Pd(PPh3)4 (0.06 g, 0.05 mmol) in DME (5 mL) was added phenylboronic acid (0.07 g, 0.60 mmol) and aqueous 2M Na2CO3 solution (0.50 mL). The reaction mixture was then heated to 85° C. for 18 h before it was poured into brine (50 mL) and extracted with EtOAc (3×100 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 1:9 Et2O/DCM) gave the title compound as a white solid (0.03 g, 19%). δH (DMSO-d6) 7.49-7.32 (5H, m), 3.57-3.54 (4H, m) 2.92-2.89 (4H, m), 2.56-2.44 (4H, m), 2.02-1.94 (2H, m). δ 13C (DMSO-d6) 189.9, 162.8, 153.9, 135.2, 129.6 (2×CH), 129.1 (2×CH), 127.8, 124.0, 123.3, 65.7 (2×CH2), 51.6 (2×CH2), 37.8, 25.8, 24.3. LCMS (ES+) 314.0 (M+H)+.

Provenance & Evidence