(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(imidazo[1,2-a]pyridin-6-yl)methanone → (Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(imidazo[1,2-a]pyridin-6-yl)ethanol

HRID 69291

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([CH:19]=[CH:20][N:21]=4)[CH:18]=3)=[O:12])=[CH:9][N:10]=2)[N:7]=1.[CH3:22][Mg]Br>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([CH:19]=[CH:20][N:21]=4)[CH:18]=3)([OH:12])[CH3:22])=[CH:9][N:10]=2)[N:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-imidazo[1,2-a]pyridin-6-yl-methanone (Stage 292.2, 4.0 g, 13.44 mmol) was suspended in dioxane (400 mL) and it was heated at 90° C. When all the material was in solution, it was cooled down to 50° C. and the 3 M methylmagnesium bromide solution (28.8 mL, 40.3 mmol) was added. It was refluxed for 2 h. Then it was cooled down to rt and the precipitate formed was filtered off. It was taken up with EtOAc/MeOH (9:1) and washed with saturated NaHCO3 solution and brine. The organic layer was dried over Na2SO4, filtered and concentrated to give the title compound as a brown solid (tR 0.3 min (conditions 2), MH+=314)

Aufarbeitung

temperaturewas cooled down to 50° C.
temperatureIt was refluxed for 2 h
temperatureThen it was cooled down to rt
customthe precipitate formed
filtrationwas filtered off
washwashed with saturated NaHCO3 solution and brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-f7c60afc4a2e46c5865e8ee3d2a3be15
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822468B2

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