Tributylphenyltin → 3-Phenyl-1H-5-indazolecarbonitrile

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Reaktionsgleichung

Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.C([Sn](CCCC)(CCCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)CCC>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]1([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=3)[NH:4][N:3]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To a solution of 300 mg of tert-butyl 3-bromo-5-cyano-1H-1-indazolecarboxylate produced in Production Example I-14-b in 10 ml dimethylformamide were added 376 mg of tri-n-butyl(phenyl)tin and 54 mg of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 150° C. for 45 minutes. After removing the solvent by distillation, the residue was dissolved in 1.5 ml of ethyl acetate and the mixture was adsorbed by 1.5 g of silica gel. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:toluene=3:97 to 1:19) and the resulting amorphous powder was crystallized from diisopropyl ether, to give 117 mg of the title compound as pale yellow crystals.

Aufarbeitung

customAfter removing the solvent
distillationby distillation
dissolutionthe residue was dissolved in 1.5 ml of ethyl acetate
customThe crude product was purified
customseparated by silica gel column chromatography (ethyl acetate:toluene=3:97 to 1:19)
customthe resulting amorphous powder was crystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag: ord-ebec3da8230a4b85932f23ec421b8491
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07776890B2

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