Ethyl Glycolate → HCID 86608509, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione (0.34 mmol, 100 mg) in dry THF (1.0 mL) under an atmosphere of N2 at room temperature was added ethyl glycolate (0.34 mmol, 35 mg). The reaction mixture was cooled to 0° C. and tributylphosphine (0.17 mmol, 34 mg) was added followed by 1,1′-(azodicarbonyl)dipiperidine (0.36 mmol, 84 mg). After stirring at 0° C. for 10 min., the reaction mixture was brought to room temperature and the stirring was continued for 26 h. The reaction mixture was diluted with CH3CN:water 1:1 (2 mL) and purified using HPLC (95% 0.1M ammonium acetate buffer:5% CH3CN→100% CH3CN, 38.5 min., 25 mL/min.) to give 53 mg (41%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.22-7.17 (bs, 1H), 7.15-7.05 (m, 3H), 7.01-6.96 (m, 2H), 6.63-6.52 (m, 4H), 4.36 (s, 2H), 4.24 (q, J=7.1 Hz, 2H), 3.69 (s, 3H), 1.30 (t, J=7.1 Hz, 3H).

Provenance & Evidence