Potassium Carbonate → HCID 22050431, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoate (from Step 1) (16.5 g, 60.4 mmol) 2,4-difluorobenzyl bromide (7.8 ml, 60.4 mmol) were taken up in 250 ml of N,N-dimethylformamide and the mixture was cooled to 0° C. K2CO3 (8.3 g, 60.4 mmol) was added and reaction stirred for 12 hours during which time the reaction was allowed to warm to room temperature. LC/MS indicated the presence of starting material after 12 hours. An excess of K2CO3 was added at room temperature along with 0.50 ml of 2,4-difluorobenzyl bromide. The reaction stirred for an additional two hours. Saturated NaHCO3 (aq.) was poured into reaction vessel. The solution was extracted with ethyl acetate and the organic layers were combined then washed with water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over Na2SO4, and evaporated. The product was carried on to the next step as a crude oil (24.1 g, quantitative yield). 1H NMR (300 MHz, CDCl3) δ 8.06 (dd, J=7.85, 1.61 Hz, 1H), 7.82 (d, J=1.61, 1H), 7.52 7.44 (m, 2H), 7.01-6.88 (m, 2H), 6.05 (d, J=2.62 Hz, 1H), 5.97 (dd, J=2.62, 0.81 Hz, 1H), 5.08 (s, 2H), 3.93 (s, 3H), 2.20 (s, 3H), 1.89 (s, 3H); ES-MS m/z 400 (M+H). ES-HRMS m/z 400.1374 (M+H calcd for C22H20F2NO4 requires 400.1355).

Provenance & Evidence