Ethyl Acetate → (1-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1H-pyrazol-3-yl)boronic acid

HRID 511344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 511344
[B:1]1([C:10]2[NH:14][N:13]=[CH:12][CH:11]=2)[O:5]C(C)(C)C(C)(C)[O:2]1.[C:15]([Si:19]([O:22][CH2:23][CH2:24]I)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.O>[Si:19]([O:22][CH2:23][CH2:24][N:13]1[CH:12]=[CH:11][C:10]([B:1]([OH:2])[OH:5])=[N:14]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:21])[CH3:20]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilaneHCID 219315393-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Produkt 1

HCID 67260822(1-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1H-pyrazol-3-yl)boronic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a sealed tube, a suspension of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-pyrazole (100.0 mg, 0.5154 mmol), tert-butyl-(2-iodoethoxy)-dimethylsilane (196 mg, 0.685 mmol), and Cs2CO3 (271 mg, 0.832 mmol) in DMF (3 mL) was stirred at 100° C. for 16 h. The sample was suspended between EtOAc and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, giving the title material as the boronic acid, as a yellow oil (203.4 mg). MS (ES+): m/z 270.18/271.13/272.15 (19/79/15) [MH+]. HPLC: tR=3.33 min (CAD, ZQ3, polar—5 min).

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5f6d142848174ee7a1a194b2ecbdfb94
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096624B2

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