Dichloromethane → 4-(1-isobutyl-1H-pyrazol-4-yl)aniline

HRID 717912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717912
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH2:9]([N:13]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[N:14]1)[CH:10]([CH3:12])[CH3:11].ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCCC1.O.CO>[CH2:9]([N:13]1[CH:17]=[C:16]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)[CH:15]=[N:14]1)[CH:10]([CH3:12])[CH3:11]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 78074-BromoanilineHCID 10340Sodium CarbonateHCID 27593921-Isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Produkt 1

HCID 633283934-(1-isobutyl-1H-pyrazol-4-yl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A suspension of 4-bromoaniline (406 mg, 2.362 mmol), 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (650 mg, 2.60 mmol), [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II), complex with dichloromethane (57.9 mg, 0.071 mmol) and sodium carbonate (526 mg, 4.96 mmol) in a 6:2:1 mixture of tetrahydrofuran/water/methanol (12 ml) in a microwave vial was subjected to three vacuum/nitrogen purge cycles. The vial was sealed and heated in an oil bath at 85° C. overnight. The mixture was dissolved in a mixture of ethyl acetate (45 ml) and water (20 ml), and the separated aqueous layer was extracted with ethyl acetate (20 ml). The combined organic layers were washed with brine (20 ml), dried with magnesium sulfate, filtered and concentrated. Normal phase chromatography provided the title compound.

Aufarbeitung

  1. custompurge cycles
  2. customThe vial was sealed
  3. dissolutionThe mixture was dissolved in a mixture of ethyl acetate (45 ml) and water (20 ml)
  4. extractionthe separated aqueous layer was extracted with ethyl acetate (20 ml)
  5. washThe combined organic layers were washed with brine (20 ml)
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-19592b8c97904945a0aa91aee2395d88
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193723B2

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