Sodium hydride → 1-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol ester

HRID 57526

Reaktionsgleichung

Reaktionsgleichung von HRID 57526
[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][CH2:17][O:18][CH3:19].[H-].[Na+]>C1COCC1>[CH3:19][O:18][CH2:17][CH2:16][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Produkt 1

HCID 112304911-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (200 mg, 1.03 mmol), 1-bromo-2-methoxyethane (280 mg, 2.01 mmol), and NaH (200 mg, 4 mmol) in THF (15 mL) was stirred at reflux for 24 hours, cooled to the ambient temperature, and concentrated in vacuo. The residue was treated with HCl(aq) and extracted with EtOAc. The insoluble solid was removed by filtration, and the organic solution was concentrated to give the title compound. MS (m/z): 253 (M+H)+.

Aufarbeitung

  1. temperatureat reflux for 24 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with HCl(aq)
  4. extractionextracted with EtOAc
  5. customThe insoluble solid was removed by filtration
  6. concentrationthe organic solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2910dcc4677c4e7985ca0045b2de53aa
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434726B2

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