P-Anisidine → 1-[(6-Aminopyridin-3-yl)methyl]-3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl {5-[(3-chloro-2,5-dioxo-4-phenyl-2,5-dihydro-1H-pyrrol-1-yl)methyl]pyridin-2-yl}carbamate (0.86 mmol, 357 mg) in dry DMF (1.0 mL) was added 4-methoxyaniline (0.96 mmol, 118 mg) and anhydrous potassium carbonate (0.96 mmol, 133 mg) and the reaction mixture was subjected to microwave heating single node at 150° C. for 15 min. The reaction mixture was purified using HPLC (95% 0.1M ammonium acetate buffer:5% CH3CN→5% 0.1M ammonium acetate buffer: 95% CH3CN, 10 min., 25 mL/min.) to give 102 mg (29%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.03 (s, 1H), 7.62 (dd, J=8.6 Hz, J=2.3 Hz, 1H), 7.21 (bs, 1H), 7.15-7.04 (m, 3H), 6.98-6.93 (m, 2H), 6.62-6.49 (m, 5H), 4.62 (s, 2H), 3.69 (s, 3H).

Provenance & Evidence