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

HRID 873568Notizen

Reaktionsgleichung

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].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].ClCCl.O1CCCC1.CO.O>[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

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), PdCl2(dppf)-dichloromethane adduct (57.9 mg, 0.071 mmol) and sodium carbonate (526 mg, 4.96 mmol) in a 6:2:1 mixture of tetrahydrofuran/methanol/water (12 ml) was taken through three vacuum/nitrogen purge cycles; and the reaction mixture was heated in an oil bath at 85° C. overnight. The mixture was diluted with ethyl acetate and water; the separated aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried with magnesium sulfate, filtered and concentrated. The residue was purified by normal phase chromatography to give the title compound.

Aufarbeitung

custompurge cycles
additionThe mixture was diluted with ethyl acetate and water
extractionthe separated aqueous layer was extracted with ethyl acetate
washthe combined organic layers were washed with brine
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by normal phase chromatography

Quellen und Nachweise

ORD-Eintrag: ord-17f19f6eeb524441b70562349a4e2f84
Quelldatensatz: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08975398B2

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