Indoline → HCID 76281598, compound

Participants

Reaction Steps

To a solution of indoline (13 μL, 0.116 mmol) in dichloroethane (1 mL) was added Na(OAc)3BH (74 mg, 0.35 mmol). The mixture was stirred at room temperature under argon for 20 min. A slurry of 3-(4-formyl-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 20; 25 mg, 0.116 mmol) in dichloroethane (1 mL) was added, followed by AcOH (20 μL). The reaction mixture was stirred at room temperature overnight. 1 M Na2CO3 solution was added and the mixture was extracted with EtOAc (3×25 mL). The organic layer was washed with brine, dried (Na2SO4), evaporated, and purified by chromatography (12.5-20% acetone/CH2Cl2) to give 3-[4-(2,3-dihydro-indol-1-ylmethyl)-phenyl]-isoxazole-5-carboxylic acid amide (24 mg, 65%), as an off-white powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.27 (br. s., 1H), 7.90 (br. s., 1H), 7.79 (d, J=8.2 Hz, 2H), 7.48 (s, 1H), 7.41 (d, J=8.2 Hz, 2H), 6.95 (d, J=6.9 Hz, 1H), 6.88 (t, J=7.7 Hz, 1H), 6.42-6.55 (m, 2H), 4.23 (s, 2H), 3.14-3.21 (m, 2H), 2.75-2.87 (m, 2H).

Provenance & Evidence