Dichloromethane → Ethyl 4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzoate
Reaktionsgleichung
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)=[O:5])[CH3:2].Br[C:16]1[CH:17]=[N:18][N:19]2[CH:24]=[CH:23][CH:22]=[N:21][C:20]=12.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O>[N:18]1[N:19]2[CH:24]=[CH:23][CH:22]=[N:21][C:20]2=[C:16]([C:9]2[CH:10]=[CH:11][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=2)[CH:17]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 85 °C
Versuchsvorschrift
Water (160 mL) was added dropwise at room temperature to a mixture of 4-ethoxycarbonylphenylboronic acid (50 g, 0.26 mol), 3-bromopyrazolo[1,5-a]pyrimidine (56.25 g, 0.28 mol), Pd(ddpf)Cl2.CH2Cl2 (4.25 g, 5.21 mmol), and Cs2CO3 (169.42 g, 0.52 mol) in 1,4-dioxane (1 L). The reaction mixture was then heated 85° C. for 4 h. The reaction mixture was cooled, poured into water and extracted with EtOAc (2×300 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with a gradient of petroleum ether: EtOAc (100:10 to 3:1) to deliver the title compound (64 g, 93%) as a yellow solid.
Aufarbeitung
- temperatureThe reaction mixture was cooled
- extractionextracted with EtOAc (2×300 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
- customThe crude product was purified by silica gel chromatography
- washeluting with a gradient of petroleum ether: EtOAc (100:10 to 3:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-151e3f75b2c54638be3ddc4985ba5cf2
- Quelldatensatz
- uspto-grants-2016_01
- Patentnummer
- US09227956B2
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