Reaktion #69793

Reaktionsgleichung

(E)-1-(tetrahydro-2H-pyran-2-yl)-3-(2-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)vinyl)-1H-indazol-5-ol

cesium carbonate

(S)-1-(3,5-dichloropyridin-4-yl)ethyl methanesulfonate

→

5-((R)-1-(3,5-Dichloropyridin-4-yl)ethoxy)-1-(tetrahydro-2H-pyran-2-yl)-3-((E)-2-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)vinyl)-1H-indazole

Lösungsmittel

ACN

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 3-neck 250 mL round bottom flask equipped with an internal temperature probe
2. 2
   Temperaturreflux condenser
3. 3
   Filtrationfilter
4. 4
   Waschenwash solids with ACN
5. 5
   EinengenConcentrate the filtrate
6. 6
   Sonstigepurify the residue by silica gel chromatography (2-4% (2 M ammonia in methanol)/DCM)
7. 7
   EinengenCombine product fractions and concentrate in vacuo to a white foam

Vorschrift

In a 3-neck 250 mL round bottom flask equipped with an internal temperature probe, reflux condenser, nitrogen blanket and magnetic stir bar, slurry (E)-1-(tetrahydro-2H-pyran-2-yl)-3-(2-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)vinyl)-1H-indazol-5-ol (10.0 g, 22.83 mmol) and cesium carbonate (7.88 g, 23.94 mmol) in ACN (92 mL) and warm to 60° C. To the suspension, add (S)-1-(3,5-dichloropyridin-4-yl)ethyl methanesulfonate (7.03 g, 26.02 mmol) and stir overnight. Cool the reaction mixture to RT, filter and wash solids with ACN. Concentrate the filtrate and purify the residue by silica gel chromatography (2-4% (2 M ammonia in methanol)/DCM). Combine product fractions and concentrate in vacuo to a white foam. Yield: 12.5 g (86%). MS (ES) m/z 612 [M+1]+.

Quelle