Potassium Carbonate → (Z)-5-(but-2-en-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

HRID 242221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 242221
[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.[CH3:18]/[C:19](/B(O)O)=[CH:20]/[CH3:21].C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[CH3:18]/[C:19](/[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])=[CH:20]/[CH3:21]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 11389361(E)-But-2-EN-2-ylboronic acidHCID 671200291-(2-fluoro-4-hydroxyphenyl)-5-iodo-3-methyl-1H-pyrazole-4-carbonitrile

Produkt 1

HCID 67120037(Z)-5-(but-2-en-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrileAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 1-(2-fluoro-4-hydroxyphenyl)-5-iodo-3-methyl-1H-pyrazole-4-carbonitrile (40 mg, 0.12 mmol), (E)-but-2-en-2-ylboronic acid (23.3 mg, 0.23 mmol), K2CO3 (96.7 mg, 0.70 mmol) and Pd(PPh3)4 (13.47 mg, 0.01 mmol) in DME (1 mL) and water (1 mL) was flushed with N2 and irradiated in the microwave at 150° C. for 10 min. Water and DCM were added and the phases were separated. The organic layer was concentrated and the crude product was purified on HPLC to give (Z)-5-(but-2-en-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (23.0 mg, 73%).

Aufarbeitung

  1. customwas flushed with N2
  2. customirradiated in the microwave at 150° C. for 10 min
  3. additionWater and DCM were added
  4. customthe phases were separated
  5. concentrationThe organic layer was concentrated
  6. customthe crude product was purified on HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6138e6c2c83d4dcb9c04884e7cbc7d4a
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653112B2

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