Sodium Carbonate → HCID 16110520, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of thiophene-3-boronic acid (53 mg, 0.42 mmol), ethyl {(1 S)-5-[3-(4-iodophenoxy)propoxy]-2,3-dihydro-1H-inden-1-yl}acetate (50 mg, 0.10 mmol, Example 94) in toluene (1.8 mL), and 1,4-dioxane (0.45 mL), was added PdCl2(dppf)-CH2Cl2 (7.6 mg, 0.01 mmol), and argon was passed through the mixture for 30 min. Then Na2CO3 (2 N aqueous solution, 0.50 mL) was added, and the mixture was heated to 75° C. for 48 h. The reaction was cooled to rt, and extracted with EtOAc (2×). The combined organic phases were washed with NaHCO3 (saturated aqueous solution), dried, filtered and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel to give 33 mg (73%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.51 (d, 2H), 7.40-7.31 (m, 3H), 7.06 (d, 1H), 6.97 (d, 2H), 6.80 (s, 1H), 6.72 (dd, 1H), 4.24-4.10 (m, 6H), 3.60-3.48 (m, 1H), 2.98-2.90 (m, 2H), 2.72 (dd, 1H), 2.46-2.36 (m, 2H), 2.36-2.23 (m, 2H), 1.85-1.70 (m, 1H), 1.30 (t, 3H).

Provenance & Evidence