Reaktionsgleichung
Br[C:2]1[CH:3]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[N:28][NH:29][CH:30]=2)O1.C([O-])(O)=O.[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:11]([N:8]1[C:9]2[CH:10]=[C:2]([C:26]3[CH:27]=[N:28][NH:29][CH:30]=3)[CH:3]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]=2[CH:6]=[N:7]1)([CH3:13])[CH3:12]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
To a stirred solution of methyl 6-bromo-1-isopropyl-1H-indazole-4-carboxylate, 1 (0.8 g, 2.7 mmol) in 1,4-dioxane (20 mL) were added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.576 g, 2.97 mmol) and NaHCO3 (0.567 g, 6.75 mmol) dissolved in water (8 mL). The reaction mixture was degassed with argon gas for 30 min. To the resulting mixture was added PdCl2(dppf)-CH2Cl2 adduct (0.110 g, 0.135 mmol) and the mixture heated at reflux for 3 h. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (100 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford 800 mg of crude product. The crude compound was purified by silica gel chromatography (eluent: 5% MeOH/DCM) to the title compound as a pale liquid (375 mg, 47%). LCMS (ES−) m/z=283.11.
Aufarbeitung
- customThe reaction mixture was degassed with argon gas for 30 min
- temperaturethe mixture heated
- temperatureat reflux for 3 h
- extractionextracted with ethyl acetate (100 mL)
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-59d4437b9537419db01ea2e1b794eb59
- Quelldatensatz
- uspto-grants-2015_04
- Patentnummer
- US09018382B2
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