Cesium carbonate → 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetamide

HRID 2090446

Reaktionsgleichung

Reaktionsgleichung von HRID 2090446
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.Br[CH2:16][C:17]([NH2:19])=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:16][C:17]([NH2:19])=[O:18])[CH:10]=2)[O:3]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 696322-BromoacetamideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Produkt 1

HCID 569657342-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (50 mg, 0.2 mmol), 2-Bromoacetamide (43 mg, 0.31 mmol, Aldrich, Cat. No. 301272), and cesium carbonate (250 mg, 0.77 mmol) in acetonitrile (1 mL) was stirred at 90° C. for 2 h. After cooling it was quenched with water, extracted with ethyl acetate. The extract was washed with water twice, brine once; dried over Na2SO4. After filtration the filtrate was concentrated to yield 45 mg of the product which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=252.1

Aufarbeitung

  1. temperatureAfter cooling it
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water twice
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration the filtrate
  7. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-681abdcfcc0648aea47dc9d7db31c577
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436008B2

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