Potassium Carbonate → tert-butyl 2-(6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-(2-hydroxyethyl)pyridin-2-yl)-3-methyl-1H-indole-1-carboxylate

Participants

Reaction Steps

To a solution of (E)-tert-butyl 2-(3-(2-ethoxyvinyl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyridin-2-yl)-3-methyl-1H-indole-1-carboxylate (72 mg, 0.096 mmol) in THF (0.350 mL) at 0° C. was added Mercuric acetate (36.6 mg, 0.115 mmol) in H2O (0.350 mL). After stirring the resultant mixture at 0° C. for 30 min, NaBH4 (14.47 mg, 0.383 mmol) in 0.580 mL of saturated (aq) K2CO3 solution was added and the reaction mixture was warmed to ambient temperature. After 1.5 h at ambient temperature, the reaction mixture was diluted with EtOAc and washed successively with H2O (2×) and brine (1×). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a gradient of 0-90% EtOAc/CH2Cl2 as eluent. 1H NMR δ (ppm) (CHCl3-d): 8.16 (1H, d, J=8.33 Hz), 8.03˜7.99 (3H, m), 7.87 (1H, d, J=7.99 Hz), 7.69˜7.65 (2H, m), 7.57 (1H, d, J=7.77 Hz), 7.39 (1H, t, J=7.73 Hz), 7.33 (1H, t, J=7.42 Hz), 7.22 (2H, t, J=8.58 Hz), 5.95 (1H, br s), 3.81 (2H, m), 3.19 (3H, s), 3.00 (3H, d, J=4.88 Hz), 2.98˜2.83 (2H, m), 2.78 (3H, s), 2.11 (3H, s), 1.45 (6H, s), 1.27 (3H, s). MS (M+H): 727.

Provenance & Evidence