Sodium Iodide → 4-(4-bromo-5-cyano-2-ethyl-2H-pyrazol-3-yl)butyl acetate

HRID 1360432

Reaktionsgleichung

[C:1]([O-:4])(=[O:3])[CH3:2].[K+].[I-].[Na+].CN(C=O)C.[Br:13][C:14]1[C:15]([C:26]#[N:27])=[N:16][N:17]([CH2:24][CH3:25])[C:18]=1[CH2:19][CH2:20][CH2:21][CH2:22]Cl>O>[C:1]([O:4][CH2:22][CH2:21][CH2:20][CH2:19][C:18]1[N:17]([CH2:24][CH3:25])[N:16]=[C:15]([C:26]#[N:27])[C:14]=1[Br:13])(=[O:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Potassium acetate (1.69 g, 17.2 mmol), sodium iodide (255 mg, 1.7 mmol), and DMF (17 mL) were added to 4-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile (1.0 g, 3.4 mmol, prepared as described in Parts A-E of Example 19), and the reaction was heated at 100° C. for two hours under a nitrogen atmosphere and allowed to cool to ambient temperature. Water was added, and the resulting mixture was extracted with diethyl ether. The combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on a HORIZON HPFC system (40+M cartridge, eluting with hexanes/ethyl acetate in a gradient from 90:10 to 60:40) to provide 0.86 g of 4-(4-bromo-5-cyano-2-ethyl-2H-pyrazol-3-yl)butyl acetate.

Aufarbeitung

temperatureto cool to ambient temperature
extractionthe resulting mixture was extracted with diethyl ether
washThe combined extracts were washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by chromatography on a HORIZON HPFC system (40+M cartridge
washeluting with hexanes/ethyl acetate in a gradient from 90:10 to 60:40)

Quellen und Nachweise

ORD-Eintrag: ord-281e0706cfe1425eaca93023ce1cf1c4
Quelldatensatz: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07879849B2

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