Oxygen → 1-Methyl-3-(pyridin-4-yl)-4-(4-(quinolin-2-ylmethoxy)phenyl)-1h-pyrrole-2,5-dione

Participants

Reaction Steps

To a stirred solution of 1-methyl-4-(pyridin-4-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrrol-2(5H)-one (200 mg, 0.49 mmol) in AcN (10 mL) was added DBU (224.5 mg, 1.47 mmol) dropwise and then the reaction mixture was stirred for 6 h under a continuous flow of oxygen. The reaction mixture was quenched with 1N HCl and extracted with EtOAc (2×20 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo to afford 1-methyl-3-(pyridin-4-yl)-4-(4-(quinolin-2-ylmethoxy)phenyl)-1H-pyrrole-2,5-dione (100 mg, 48%) as a solid 1H NMR (500 MHz, CDCl3): δ 8.18-8.09 (m, 1 H), 8.0-7.95 (m, 3 H), 7.65-7.59 (m, 3 H), 7.48-7.39 (m, 1 H), 7.28-7.18 (m, 4 H), 7.1-7.09 (m, 2 H), 5.25 (s, 2 H), 2.86 (s, 3H); MS: M−H: m/z=420.1.

Provenance & Evidence