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Potassium Carbonate → 2-{4-[3,5-Dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethanol

HRID 891075
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 891075
I[C:2]1[C:3]([CH3:17])=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[C:6]=1[CH3:7].B(O)(O)[C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>C(COC)OC.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>[CH3:17][C:3]1[C:2]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[C:6]([CH3:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[N:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 222445592-[4-(4-Iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol

Produkt 1

HCID 222445852-{4-[3,5-Dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, Verbindung
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-[4-(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol (step 2 of Example 11, 300 mg, 0.88 mmol) and p-tolylboronic acid (313 mg, 2.3 mmol) in dimethoxyethane (6.3 mL) were added 2 M aqueous K2CO3 (2.2 mL, 4.4 mmol) and bis(triphenylphosphine)palladium(II) chloride (124 mg, 0.18 mmol), and the mixture were refluxed for 16 h. The mixture was filtered through a pad of Celite and the filtrate was concentrated to give brown oil. It was partitioned between dichloromethane and water. The separated organic layer was dried (Na2SO4), evaporated, and purified by TLC with hexane/ethyl acetate (1:1) to afford 349 mg (quant.) of the title compound as white solids: MS (ESI) m/z 307 [M+H]+, 1H-NMR (CDCl3) δ 7.43-7.20 (8H, m), 3.87 (2H, t, J=6.4 Hz), 2.91 (2H, t, J=6.4 Hz), 2.40 (3H, s), 2.31 (3H, s), 2.28 (3H, s).

Aufarbeitung

  1. temperaturethe mixture were refluxed for 16 h
  2. filtrationThe mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated
  4. customto give brown oil
  5. customIt was partitioned between dichloromethane and water
  6. dry with materialThe separated organic layer was dried (Na2SO4)
  7. customevaporated
  8. custompurified by TLC with hexane/ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-6f18d4f98fa448e5b29bf5003383b6ab
Quelldatensatz
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07001917B2

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