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

HRID 1802892

Reaktionsgleichung

CON(C)[C:4](=[O:24])[CH:5]([N:13]1[C:17]2=[N:18][CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:16]2[CH:15]=[N:14]1)[CH2:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH:26]([Mg]Br)=[CH2:27].Cl>O1CCCC1>[CH3:23][O:22][C:21]1[CH:20]=[CH:19][N:18]=[C:17]2[N:13]([CH:5]([CH2:6][CH:7]3[CH2:8][CH2:9][O:10][CH2:11][CH2:12]3)[C:4](=[O:24])[CH:26]=[CH2:27])[N:14]=[CH:15][C:16]=12

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

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+).

Aufarbeitung

customat 0° C.
stirringthe mixture was stirred for 1 hr under ice-
temperaturecooling
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-67367a155c5f450087c1dfb99ba6aac4
Quelldatensatz: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08349886B2

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