Reaktion #675358

Reaktionsgleichung

cesium carbonate

6-Chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

(R)-1-(1-phenylethyl)urea

BrettPhos

→

(R)-1-(3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was evacuated
2. 2
   workup.ADDITIONback-filled with N2 (×3)
3. 3
   FiltrationThe reaction mixture was filtered through Celite
4. 4
   Wascheneluting with MeOH
5. 5
   Einengenthe filtrate was concentrated in vacuo
6. 6
   SonstigePurification of the residue by flash chromatography (12-100% EtOAc-hexanes)

Vorschrift

6-Chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (133 mg, 0.312 mmol), (R)-1-(1-phenylethyl)urea (115 mg, 0.700 mmol), 1:1 BrettPhos:BrettPhos pre-catalyst (20.5 mg, 0.015 mmol), and cesium carbonate (254 mg, 0.781 mmol) were taken up in 1,4-dioxane (3 mL) in a 5 mL microwave vial. The vial was evacuated and back-filled with N2 (×3) and the reaction stirred at 100° C. for 6 h. The reaction mixture was filtered through Celite, eluting with MeOH, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (12-100% EtOAc-hexanes) gave (R)-1-(3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. For C35H31N5O2 [M+1]+ 554. found 554.

Quelle