Sodium hydride → HCID 76282126, compound

Participants

Reaction Steps

To a mixture of 4-methylindole (20 mg, 0.15 mmol) in THF (1 mL) was added NaH (60% dispersion; 5 mg, 0.125 mmol). The mixture was stirred for 30 min and then a solution of 3-(4-bromomethyl-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 14; 35 mg, 0.125 mmol) in THF (1 mL) was added. The reaction mixture was stirred at room temperature overnight. The THF was evaporated and the residue was taken up in DMF (2 mL). The reaction mixture was stirred at room temperature for 8 days, then H2O was added and the mixture was extracted with EtOAc (3×25 mL). The combined organic layers were washed three times with H2O/brine, dried (Na2SO4), evaporated, and purified by chromatography (16-20% acetone/CH2Cl2) to give 3-[4-(4-methyl-indol-1-ylmethyl)-phenyl]-isoxazole-5-carboxylic acid amide (6 mg, 14%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.35 (br. s., 1H), 7.97 (br. s., 1H), 7.81 (d, J=8.2 Hz, 2H), 7.43-7.56 (m, 2H), 7.17-7.34 (m, 3H), 6.91-7.03 (m, 1H), 6.80 (d, J=6.9 Hz, 1H), 6.51 (d, J=3.0 Hz, 1H), 5.47 (s, 2H), 2.45 (s, 2H).

Provenance & Evidence