Sodium Carbonate → 2-(4-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)phenyl)-2-methylpropanenitrile

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Reaction Steps

3-(1H-Benzo[d]imidazol-2-yl)-5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (20 mg, 0.050 mmol), [4-(1cyano-1-methylethyl)phenyl]boronic acid (10 mg, 0.074053 mmol) and triphenylphosphine (2 mg, 0.007 mmol) were dissolved in a mixture of THF (6 mL) and 1M Na2CO3 (aq) (10 mg, 0.094 mmol). Palladium acetate (1 mg, 0.004 mmol) was added and the solution was heated overnight at reflux. After cooling to room temperature, and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (25 mL) and washed with water (20 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (25 mL). The combined organic layers were washed with brine (20 mL), dried over Na2SO4, and concentrated. Purification by flash chromatography (20% ethyl acetate/hexane) afforded the title compound (7 mg). 1H NMR (400 MHz, CDCl3): δ 8.79 (s, 1H), 7.80 (bs, 1H), 7.75 (m, 2H), 7.70 (m, 1H), 7.64 (m, 1H), 7.53-7.48 (m, 3H), 7.25-7.22 (m, 2H), 5.76 (d, 1H, J=8.4 Hz), 4.06 (m, 1H), 3.77 (m, 1H), 2.55 (m, 1H), 2.10 (m, 2H), 1.73 (m, 3H), 1.72 (s, 6H).

Provenance & Evidence