Cesium carbonate → 3-(Benzyloxy)-1-methyl-5-(4-phenyl-1H-imidazol-1-yl)pyridin-2(1H)-one

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

3-(Benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one (50 mg, 0.170 mmol), 4-phenylimidazole (29 mg, 0.201 mmol), Cs2CO3 (111 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 DMF (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 6 h the mixture was cooled to RT. The mixture was filtered using a 0.45 μm PTFE syringe filter then purified by preparative reversed-phase HPLC (20×150 mm Waters Sunfire (0.1% TFA), 5-50% CH3CN/water over 20 min at 20 mL/min). Fractions containing the product were pooled then passed through Dowex 1×2-400 ion exchange resin (prewashed with 1M NaOH, H2O, MeOH) washing with MeOH. The filtrate was concentrated to give the title compound (32 mg, 53%) as an amber film. 1H NMR (500 MHz, CDCl3): δ 7.78 (d, J=7.7 Hz, 2 H); 7.59 (s, 1 H); 7.45-7.36 (m, 9 H); 7.13 (d, J=2.5 Hz, 1 H); 6.73 (d, J=2.5 Hz, 1 H); 5.19 (s, 2 H); 3.65 (s, 3 H). LC/MS (M+H)+ 358.

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