N,N'-Dimethylethylenediamine → 3-(Benzyloxy)-1-methyl-5-(2-oxo-4-phenylpyrrolidin-1-yl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

3-(Benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one (100 mg, 0.340 mmol), 4-phenylpyrrolidin-2-one (71 mg, 0.440 mmol), K3PO4 (144 mg, 0.680 mmol), CuI (4 mg, 0.021 mmol), and N,N′-dimethylethylenediamine (5 μl, 0.046 mmol) were combined in 1,4-dioxane (1 mL) in a screw cap vial. The vial was sealed then heated to 110° C. After heating overnight the mixture was cooled to RT and diluted with CH2Cl2. The resulting mixture was filtered through a pad of Celite®, washing with CH2Cl2, and concentrated. Flash column (Biotage-SNAP-25 g, 0-10% MeOH/CH2Cl2) gave the title compound (131 mg, 103%) as an off-white foam which was sufficiently pure for use in the next step. 1H NMR (500 MHz, CDCl3): δ 7.44-7.24 (m, 11 H); 7.09 (s, 1 H); 5.15 (s, 2 H); 3.97 (s, 1 H); 3.71-3.65 (m, 2 H); 3.59 (s, 3 H); 3.00-2.92 (m, 1 H); 2.74 (dd, S=16.9, 8.1 Hz, 1 H). LC/MS (M+H)+ 375.

Provenance & Evidence