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 242222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 242222
[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-ae917c00eb0f4070974e4bc1643675b5
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653112B2

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