Sodium Carbonate → 3-(1H-benzo[d]imidazol-2-yl)-5-(3-(methylsulfonyl)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

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Reaction Steps

3-(1H-Benzo[d]imidazol-2-yl)-5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (30 mg, 0.0755 mmol), 3-(methylsulfonyl)phenyl boronic acid (15 mg, 0.075 mmol) and triphenylphosphine (2 mg, 0.007 mmol) were dissolved in a mixture of THF (6 mL), and 1M sodium carbonate (8 mg, 0.075 mmol) and palladium (II) acetate (2 mg, 0.009 mmol) were added. The solution was heated overnight at reflux. After cooling to room temperature, the solvent was removed in vacuo, the residue was dissolved in ethyl acetate (20 mL), and washed with water (10 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layers were washed with brine (25 mL), dried over Na2SO4, and concentrated. Purification by flash chromatography (20% ethyl acetate/hexane) afforded the title compound (8 mg) as a white solid. 1H NMR (400 MHz, CDCl3): δ 9.93 (s, 1H), 8.83 (s, 1H), 8.19 (s, 1H), 7.97 (d, 1H, J=8.0 Hz), 7.86 (m, 2H), 7.61 (t, 1H, J=7.6 Hz), 7.45 (m, 1H), 7.24 (m, 4H), 5.77 (dd, 1H, J=2.4 and 9.6 Hz), 4.04 (m, 1H), 3.75 (m, 1H), 3.07 (s, 3H), 2.59 (m, 1H), 2.12 (m, 2H), 1.76 (m, 3H); ESI-MS [M+H]+: 473.3.

Provenance & Evidence