Reaktion #677976

Reaktionsgleichung

cesium carbonate

6-Chloro-N-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine

(R)-1-(1-(4-fluorophenyl)ethyl)urea

Intermediate 20C

(R)-1-(1-(4-fluorophenyl)ethyl)urea

→

(R)-1-(1-(4-fluorophenyl)ethyl)-3-(3-(methylamino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was evacuated
2. 2
   workup.ADDITIONback-filled with N2 (×3)
3. 3
   SonstigeRoom temperature
4. 4
   Filtrationthe reaction mixture was filtered through Celite
5. 5
   Wascheneluting with MeOH
6. 6
   Einengenthe filtrate was concentrated in vacuo
7. 7
   SonstigePurification of the residue by flash chromatography (0-100% EtOAc-DCM)

Vorschrift

6-Chloro-N-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine (332 mg, 0.781 mmol), (R)-1-(1-(4-fluorophenyl)ethyl)urea (Intermediate 20C; 193 mg, 1.059 mmol), BrettPhos pre-catalyst (48.0 mg, 0.060 mmol), and cesium carbonate (759 mg, 2.330 mmol) were taken up in 1,4-dioxane (6 mL) in a 20 mL microwave vial. The vial was evacuated and back-filled with N2 (×3) and the reaction was stirred at 100° C. for 3 h. Room temperature was attained, the reaction mixture was filtered through Celite, eluting with MeOH, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (0-100% EtOAc-DCM) gave (R)-1-(1-(4-fluorophenyl)ethyl)-3-(3-(methylamino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea. MS ESI calc'd. For C35H31FN6O [M+1]+ 571. found 571.

Quelle