Hydrochloric Acid → 4-[4-(cyclopropylsulfonyl)-1H-indazol-1-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[4-(cyclopropylsulfonyl)-1H-indazol-1-yl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (2.30 g) in tetrahydrofuran (20 ml) was slowly added vinylmagnesium bromide (1.0M tetrahydrofuran solution: 16.4 mL) at 0° C., and the mixture was stirred at 0° C. for 20 min. The reaction mixture was poured into an ice-cooled 1M 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 (1.80 g, yield 84%) as a colorless oil from the fraction eluted with ethyl acetate-hexane (3:1, volume ratio). MS: 389 (MH+).

Provenance & Evidence