Hydrochloric Acid → 4-(4-methoxy-1H-pyrazolo[3,4-b]pyridin-1-yl)-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of N-methoxy-2-(4-methoxy-1H-pyrazolo[3,4-b]pyridin-1-yl)-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (0.37 g) in dry tetrahydrofuran (15 mL) was slowly added vinylmagnesium bromide (1.0M tetrahydrofuran solution: 7.8 mL) at 0° C., and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added again vinylmagnesium bromide (1.0M tetrahydrofuran solution: 2.6 mL) at 0° C., and the mixture was stirred for 1 hr under ice-cooling. The reaction solution was poured into an ice-cooled 6M hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to give the title compound (0.178 g, yield 53%) as a pale-pink oil from the fraction eluted with ethyl acetate-hexane (6:4, volume ratio). MS: 316 (MH+).

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