Potassium Carbonate → HCID 59380348, compound

Participants

Reaction Steps

To a mixture of the compound from step 1 (140 mg, 0.3 mmol), thiophene-3-boronic acid (70 mg, 055 mmol), palladium(II) acetate (20 mg, 0.09 mmol) and triphenyl phosphine (40 mg, 0.18 mmol) in DME (5 mL) was added potassium carbonate (140 mg, 1 mmol), ethanol (0.5 mL) and water (0.5 mL). The mixture was stir at rt under Ar for 30 min and then was heated to 80° C. for 16 h. After cooling to rt temperature, the mixture was poured onto 20 mL ice-water, followed by extraction with EtOAc (3×10 mL). The combined organic layers were washed with water (2×10 mL), brine (10 mL) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to obtain the crude product, which was purified by silica gel flash chromatography (1% MeOH in CH2Cl2) to afford the title product (45 mg, 35%): MS (ESI) m/z 423 (M+H); 1H NMR (400 MHz, CDCl3) δ 2.56 (t, J=7.2 Hz, 2H), 2.64 (t, J=4.8 Hz, 4H), 2.77 (t, J=7.2 Hz, 2H), 3.16 (t, J=4.8 Hz, 4H), 3.70 (s, 3H), 6.90-6.99 (m, 6H), 7.34-7.37 (m, 3H), 7.51 (m, 2H).

Provenance & Evidence