Ethyl Acetate → 2-Ethyl-3-[[2-(1-methyl-1h-pyrazol-4-yl)-4-pyridinyl]oxy]-6-nitropyridine

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Reaktionsgleichung

Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH2:18][CH3:19])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH3:20][N:21]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[N:22]1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:18]([C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:24]3[CH:23]=[N:22][N:21]([CH3:20])[CH:25]=3)[CH:7]=2)=[CH:14][CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[N:11]=1)[CH3:19]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine (1.0 g, 3.6 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.0 g, 4.6 mmol) were dissolved in dioxane (10 mL). A solution of K2CO3 (1.5 g, 10.6 mmol) in water (2 mL) was added and the mixture was sonicated and sparged with Ar for 10 min. Pd(PPh3)4 (0.21 g, 0.18 mmol) was added and the reaction mixture was stirred at 80° C. for 24 h. EtOAc (60 mL) was added and the mixture was washed with sat. NaHCO3 (aq) (60 mL) and brine (60 mL), dried (Na2SO4), and concentrated in vacuo to afford 2-ethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (1.2 g, 100%) as a brown viscous oil that was carried forward without further purification. MS (ESI) m/z: 326.1 (M+H+).

Aufarbeitung

customthe mixture was sonicated
customsparged with Ar for 10 min
washthe mixture was washed with sat. NaHCO3 (aq) (60 mL) and brine (60 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-b84a06c9186246de9ce80d8f05923dd7
Quelldatensatz: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09193719B2

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