Sodium hydride → HCID 136342118, compound

Participants

Reaction Steps

A mixture of sodium hydride (330 mg, 8.2 mmol, 60% dispersion in oil, pre-washed with hexane) in N,N-dimethylformamide (2 mL) was added to 5-cyanooxindole (980 mg, 6.2 mmol) in N,N-dimethylformamide (4 mL). The formed brown mixture was stirred at room temperature for 20 min and 6-chloro-N-[2-(dimethylamino)ethyl]-N-methylnicotinamide (500 mg, 2.1 mmol) in N,N-dimethylformamide (3 mL) was added. The obtained red solution was heated at 150° C. for 30 min and was then allowed to reach room temperature overnight. The solvent was removed in vacuo and the residue was partitioned between a 2 M aqueous HCl solution and ethyl acetate. The mixture was alkalized to pH 8 by adding NaHCO3 (s) and extracted with ethyl acetate. The combined extracts were dried (Na2SO4) and the solvent was removed in vacuo to afford 450 mg of a crude product. The residue was purified on a silica gel column using chloroform/methanol/conc. NH3(aq), (80:19:1), as the eluent. Fractions containing product were collected, evaporated in vacuo and dried at 25° C. in vacuo to afford 70 mg. The residue was purified by preparative HPLC (column: Xterra, 19×300 mm, eluent: 0.05 M NH4OAc buffert/acetonitrile, 9:1-3:7). Fractions containing product were collected, evaporated in vacuo and dried at 25° C. in vacuo to afford 35 mg (4.6% yield) of the title compound as the base: 1H NMR (D2O, 400 MHz) δ 7.89 (s, 1 H), 7.59 (d, J=9 Hz, 1 H), 6.96 (s, 1 H), 6.92 (d, J=8 Hz, 1 H), 6.84 (d, J=9 Hz, 1 H), 6.65 (d, J=8 Hz, 1 H), 3.76 (s, 2 H), 3.30 (s, 2 H), 3.07 (s, 3 H), 2.84 (s, 6 H).

Provenance & Evidence