Sodium Carbonate → 3-(3,5-Dichlorophenyl)pyridine

HRID 1670465

Reaktionsgleichung

Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[CH:3]=1.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12](B2OC(C)(C)C(C)(C)O2)[CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.C(OCC)(=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>[Cl:9][C:4]1[CH:3]=[C:2]([C:12]2[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=2)[CH:7]=[C:6]([Cl:8])[CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Synthesized according to General Procedure 36. A mixture of 1-bromo-3,5-dichloro-benzene (424 mg, 1.88 mmol), 3-pyridineboronic acid pinacol ester (500 mg, 2.44 mmol), aqueous 2M Na2CO3 (1.96 mL, 3.93 mmol) and Pd(PPh3)4 (89 mg, 4 mol %) in anhydrous toluene (18 mL) was stirred overnight at 80° C. under nitrogen. The reaction was cooled down to room temperature, diluted with water (5 ml) and ethyl acetate (10 ml). The organic phase was separated, dried (Na2SO4), filtered and concentrated under reduced pressure to give a pale yellow oil, which was purified by silica-gel column chromatography to give 3-(3,5-dichlorophenyl)pyridine (481 mg, 74%) as a white solid. 1H-NMR (400 MHz, CDCl3) δ 8.81 (d, J=2.1 Hz, 1H), 8.65 (dd, J=1.4, 4.8 Hz, 1H), 7.85-7.82 (m, 1H), 7.46 (d, J=1.8 Hz, 2H), 7.41-7.38 (m, 2H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=224.3; tR=1.21 min.

Aufarbeitung

customSynthesized
temperatureThe reaction was cooled down to room temperature
customThe organic phase was separated
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a pale yellow oil, which
customwas purified by silica-gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-a2c415552ea54940a8c385187750ed78
Quelldatensatz: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07994166B2

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