1-(2-fluoro-4-hydroxyphenyl)-5-iodo-3-methyl-1H-pyrazole-4-carbonitrile → 5-(2,4-dimethylthiophen-3-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

HRID 1410169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1410169
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13](I)=[C:12]([C:15]#[N:16])[C:11]([CH3:17])=[N:10]1.C([Sn](CCCC)(CCCC)[C:23]1[C:27]([CH3:28])=[CH:26][S:25][C:24]=1[CH3:29])CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:29][C:24]1[S:25][CH:26]=[C:27]([CH3:28])[C:23]=1[C:13]1[N:9]([C:3]2[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=2[F:1])[N:10]=[C:11]([CH3:17])[C:12]=1[C:15]#[N:16]

Komponenten

4

Edukt 2

HCID 671200291-(2-fluoro-4-hydroxyphenyl)-5-iodo-3-methyl-1H-pyrazole-4-carbonitrileHCID 67120033Tributyl(2,4-dimethylthiophen-3-yl)stannane

Produkt 1

HCID 671200575-(2,4-dimethylthiophen-3-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrileAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418476HCID 178418476, VerbindungKatalysator

Versuchsvorschrift

1-(2-fluoro-4-hydroxyphenyl)-5-iodo-3-methyl-1H-pyrazole-4-carbonitrile (40 mg, 0.12 mmol), tributyl(2,4-dimethylthiophen-3-yl)stannane (140.3 mg, 0.35 mmol) and PdCl2(PPh3)2 (24.55 mg, 0.03 mmol), were mixed with 0.5 mL degassed dioxane and 0.5 mL degassed DME under nitrogen in a microwave vial. The reaction was run at 145° C. in the microwave for 30 min. Water was added, the mixture was extracted with CH2Cl2 and the organic layer was concentrated. The crude product was purified on HPLC to give 5-(2,4-dimethylthiophen-3-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (13 mg, 34%).

Aufarbeitung

  1. customdegassed dioxane and 0.5 mL
  2. customdegassed DME under nitrogen in a microwave vial
  3. additionWater was added
  4. extractionthe mixture was extracted with CH2Cl2
  5. concentrationthe organic layer was concentrated
  6. customThe crude product was purified on HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c53a1a088fa449ad9b7d4cc234faa3af
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921402B2

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