Sodium Carbonate → HCID 10166393, compound

Participants

Reaction Steps

A mixture of Example 3C (105 mg, 0.2 mmol), 4-bromo-1-iodobenzene (140 mg, 0.5 mmol), Pd2(dba)3 (18 mg, 0.04 mmol), triphenylarsine (36 mg, 0.12 mmol) and 1M Na2CO3 (0.5 mL) in dioxane (4 mL) was heated to 95° C. and stirred for 5 hours. The mixture was diluted with ethyl acetate (50 mL), washed sequentially with 1M HCl (5 mL), water (5 mL), and brine (5 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)) m/e 556 (M−H)−; 1H NMR (400 MHz, DMSO-d6) δ 8.53 (d, 1H), 8.16 (d, 1H), 7.95 (d, 2H), 7.91 (dd, 1H), 7.68-7.60 (m, 5H), 4.12 (d, 1H), 3.67 (m, 1H), 2.00-1.31 (m, 10H).

Provenance & Evidence