反应详情

温度

-10 °C

To a solution of isopropylmagnesium chloride (2 M in THF, 2.04 mL) was added LiCl (173 mg, 4.08 mmol) and the resulting solution was stirred for 1 h. THF (3 mL) was added to this solution, cooled to −10° C. Solid 3-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one (400 mg, 1.36 mmol) was added and stirred for 1 h. Trimethylborate (0.456 mL, 4.08 mmol) was added to the reaction mixture, stirred at −10° C. for 1 h and then quenched with cone HCl (0.6 mL). The cooling bath was removed, stirred at room temperature overnight and concentrated. Purification by preparative HPLC (5-95% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 276 mg [5-(benzyloxy)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl]boronic acid (78%) as a white solid. LC/MS (M+H)+260.2.

1. stirringstirred for 1 h
2. stirringstirred at −10° C. for 1 h
3. customquenched with cone HCl (0.6 mL)
4. customThe cooling bath was removed
5. stirringstirred at room temperature overnight
6. concentrationconcentrated
7. customPurification
8. additionby preparative HPLC (5-95% CH3CN/H2O over 20 min, 0.05% added TFA)