Diethyl Ether → 3-(2-Bromophenyl)-5-chloro-2-(benzyloxy)pyridine

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Reaktionsgleichung

[CH2:1]([O:8][C:9]1[C:14](Br)=[CH:13][C:12]([Cl:16])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>C1(C)C=CC=CC=1.C(O)C.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.O>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:14]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:10][CH:11]=[C:12]([Cl:16])[CH:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

2-(Benzyloxy)-3-bromo-5-chloropyridine (150 mg, 0.5 mmol) and 2-bromophenylboronic acid (100 mg, 0.5 mmol) were dissolved in toluene/ethanol (1:1, 5 ml) under nitrogen. Potassium carbonate (550 mg, 4 mmol) was added, followed by tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol). The resulting mixture was heated at 70° C. in a Smithcreator® microwave for 10 minutes. After cooling, diethyl ether(10 ml) and water (10 ml) were added, The organic layer was washed with water, dried (MgSO4) and evaporated. The product was purified by flash chromatography (silica gel, 2% ethyl acetate:isohexane) to give the title compound as a clear oil (80 mg).

Aufarbeitung

temperatureAfter cooling
washThe organic layer was washed with water
dry with materialdried (MgSO4)
customevaporated
customThe product was purified by flash chromatography (silica gel, 2% ethyl acetate:isohexane)

Quellen und Nachweise

ORD-Eintrag: ord-0619a99b59864bf8a00077c1d42ed192
Quelldatensatz: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07446222B2

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