Reaktionsgleichung
I[C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH:6]=1.C([Mg]Cl)(C)C.CO[B:23]1[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]1.[Cl-].[NH4+]>C1COCC1>[O:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[O:9][CH2:8][CH2:7][N:5]1[CH:6]=[C:2]([B:23]2[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]2)[CH:3]=[N:4]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 4-iodo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazole (8.7 g, 27.1 mmol) in THF (75 mL) at 0° C. under argon was added isopropylmagnesium chloride as a 2 M solution in THF (27.1 mL, 54.3 mmol). The reaction was stirred for 1 h at 0° C. To it was added 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.7 mL, 40.7 mmol) and the mixture was stirred for an additional 1 h while allowing to warm to room temperature. It was then treated with saturated ammonium chloride (100 mL) solution and the product was extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried over sodium sulfate, and filtered. Crude material was concentrated under reduced pressure to afford 7.1 g (81%) of 1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole as a clear yellow oil. The material was taken on crude to the next step. MS m/z=323.2 [M+1]+. Calc'd for C16H27BN2O4: 322.2
Aufarbeitung
- stirringthe mixture was stirred for an additional 1 h
- temperatureto warm to room temperature
- extractionthe product was extracted with EtOAc (3×100 mL)
- washThe combined organics were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationCrude material was concentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-c6cdfffdd95342e3b7064ebb7b145c2a
- Quelldatensatz
- uspto-grants-2012_06
- Patentnummer
- US08198448B2
Verknüpfte Notizen
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