Potassium Carbonate → 3-(Benzyloxy)-1-methyl-5-(3-phenyl-1H-pyrazol-1-yl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

3-(Benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one (50 mg, 0.170 mmol), 3-phenyl-1H-pyrazole (29 mg, 0.201 mmol), K2CO3 (47.0 mg, 0.340 mmol), CuI (2 mg, 10.50 μmol), and N,N′-dimethyl-1,2-cyclohexanediamine (6 μl 0.038 mmol) were combined in 1,4-dioxane (0.5 mL) in a screw cap vial. The vial was sealed then heated to 110° C. After stirring overnight the mixture was cooled to RT. CuI (2 mg) and N,N′-dimethyl-1,2-cyclohexanediamine (6 uL) were added and heating continued at 110° C. After stirring overnight the mixture was cooled to RT and diluted with EtOAc. The resulting mixture was filtered and concentrated. The crude material was purified by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-70% CH3CN/water over 20 min at 20 mL/min) to give the title compound (33 mg, 54%) as an amber film. 1H NMR (500 MHz, CDCl3): δ 7.85 (d, J=7.7 Hz, 2 H); 7.61 (d, J=2.5 Hz, 1 H); 7.50-7.32 (m, 9 H); 7.12 (d, J=2.6 Hz, 1 H); 6.73 (d, J=2.5 Hz, 1 H); 5.21 (s, 2 H); 3.68 (s, 3 H). LC/MS (M+H)+ 358.

Provenance & Evidence