Sodium hydride → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-1H-pyrazole
Reaktionsgleichung
Br[CH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH3:13][C:14]1([CH3:26])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:22]=[N:23][NH:24][CH:25]=2)[O:15]1.[H-].[Na+]>CN(C)C=O>[CH3:13][C:14]1([CH3:26])[C:18]([CH3:19])([CH3:20])[O:17][B:16]([C:21]2[CH:25]=[N:24][N:23]([CH2:2][C:3]34[CH2:12][CH:7]5[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]5)[CH2:4]3)[CH2:10]4)[CH:22]=2)[O:15]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A mixture of 1-(bromomethyl)adamantane (0.458 g) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.377 g) in N,N-dimethylformamide (5 mL) was cooled to 0° C. To this solution was added 60% sodium hydride (0.096 g). The solution was heated at 70° C. overnight. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 25% ethyl acetate in hexanes to provide the title compound.
Aufarbeitung
- temperatureThe solution was heated at 70° C. overnight
- customThe reaction mixture was partitioned between water and ethyl acetate
- extractionThe aqueous layer was extracted with additional ethyl acetate twice
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash column chromatography on silica gel eluting with 25% ethyl acetate in hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-7f7ece2985134599a86154a5229b4b79
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08889675B2
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