Ammonium Chloride → Methyl-[5-(4-chlorophenyl)-3-methyl-1-(pyrimidin-5-yl)-1h-pyrazol-4-yl]acetate

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Reaktionsgleichung

[F-].[Cs+].CC(C)([O-])C.[K+].[CH3:9][O:10][C:11](=[O:26])[CH2:12][C:13]1[C:14]([CH3:25])=[N:15][NH:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.[N:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1.[Cl-].[NH4+]>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:9][O:10][C:11](=[O:26])[CH2:12][C:13]1[C:14]([CH3:25])=[N:15][N:16]([C:31]2[CH:32]=[N:27][CH:28]=[N:29][CH:30]=2)[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

0.287 g (2 mmol) of cesium fluoride, 0.103 g (1 mmol) of copper(II) acetate and 0.212 g (2 mmol) of potassium tert-butoxide were added to 0.5 g (2 mmol) of methyl[5-(4-chlorophenyl)-3-methyl-1H-pyrazol-4-yl]acetate in 10 ml of dichloromethane. 0.234 g (2 mmol) of 5-pyrimidinylboronic acid was then added, and the mixture was stirred at 20° C. for 45 h. The mixture was then added to saturated ammonium chloride solution (10 ml) and extracted with dichloromethane. The combined organic phases were dried with magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC. This gave 0.040 g of product (5.8% of theory).

Aufarbeitung

extractionextracted with dichloromethane
dry with materialThe combined organic phases were dried with magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-e5415bb0317048769b49d3787c39ea4c
Quelldatensatz: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08298994B2

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