1-(2-Hydroxyethyl)-1H-pyrazole → 5-(1,3-Dioxolan-2-yl)-3-[2-(1H-pyrazol-1-yl)ethoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

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Reaktionsgleichung

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2I.[N:24]1([CH2:29][CH2:30][OH:31])[CH:28]=[CH:27][CH:26]=[N:25]1>C1(C)C=CC=CC=1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:10]=[C:9]2[O:31][CH2:30][CH2:29][N:24]1[CH:28]=[CH:27][CH:26]=[N:25]1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

The title compound was prepared from 300 mg (0.672 mmol) 5-(1,3-dioxolan-2-yl)-3-iodo-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-indazole (Example 6A) in analogy to the procedure described in Example 21A. The procedure was modified by using 5 equivalents of 2-(1H-pyrazol-1-yl)-ethanol as the alcohol reactant and by switching to toluene as solvent. The reaction mixture was heated to 140° C. for 2 h using microwave irradiation, after which time the same amounts of catalyst and ligand were added again. This cycle was repeated one more time. The crude product thus obtained was purified by preparative RP-HPLC (acetonitrile/water gradient) to afford 153 mg (52% of th.) of the title compound.

Aufarbeitung

custommicrowave irradiation
additionafter which time the same amounts of catalyst and ligand were added again
customThe crude product thus obtained

Quellen und Nachweise

ORD-Eintrag: ord-25444444e97f4654961443b38a90f509
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08551989B2

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