Sodium hydride → HCID 136342117, compound

Participants

Reaction Steps

To a solution of 5-cyanooxindole (411 mg, 2.60 mmol) in N,N-dimethylformamide (4 mL) was added sodium hydride (181 mg, 4.52 mmol, 60% dispersion in oil). After 10 min, a solution of 4-(2-[(6-chloropyrimidin-4-yl)oxy]ethyl )morpholine (367 mg, 1.51 mmol) in N,N-dimethylformamide (1.5 mL) was added dropwise. The mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo, and the residue was suspended in a 2 M aqueous HCl solution and washed twice with ethyl acetate. The aqueous layer was alkalized to pH 8 by adding a 45% aqueous NaOH solution. The obtained suspension was extracted twice with ethyl acetate. The combined phases were washed with brine, dried (Na2SO4) and the solvent was removed in vacuo. The crude product was purified on a silica gel column using chloroform/ethanol, (9:1), to chloroform/methanol, (8:2), as the eluent affording 172 mg (31% yield) of the title compound as a yellow solid: 1H NMR (DMSO-d6, 400 MHz) δ 10.89 (br s, 1 H), 8.62 (s, 1 H), 8.02 (s, 1 H), 7.30 (d, J=7 Hz, 1 H), 6.97 (d, J=8 Hz, 1 H), 6.83 (br s, 1 H), 4.52 (t, J=5 Hz, 2 H), 3.60 (t, J=4 Hz, 4 H), 2.77 (m, 2 H), 2.54 (m, 4 H); MS (TSP) m/z 366 (M++1).

Provenance & Evidence