Cesium carbonate → 3-(3-Bromo-5-chlorophenoxy)-4-methylpyridine-2-carbonitrile

HRID 505560

Reaktionsgleichung

F[C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[Br:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([Cl:18])[CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:11][C:12]1[CH:13]=[C:14]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:19][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A mixture of 3-fluoro-4-methylpyridine-2-carbonitrile (2.1 g, 15.43 mmol), 3-bromo-5-chlorophenol (3.68 g, 17.74 mmol) and cesium carbonate (5.03 g, 15.43 mmol) in DMF (30 mL) was heated at 70° C. for 1 hour and then at 80° C. for another hour, after which the mixture was partitioned between water (300 mL) and ethyl acetate (2×500 mL). The combined extracts were washed with water (100 mL) and then brine (100 mL), dried over MgSO4, filtered, and the solvent removed in vacuo. The residue was chromatographed using RediSep column (330 g) and eluted with a gradient of 0-10% EtOAc/CH2Cl2 and the pure fractions combined and concentrated on the rotary evaporator to give the title compound. LRMS (M+1)=324.9.

Aufarbeitung

waitat 80° C. for another hour
customafter which the mixture was partitioned between water (300 mL) and ethyl acetate (2×500 mL)
washThe combined extracts were washed with water (100 mL)
dry with materialbrine (100 mL), dried over MgSO4
filtrationfiltered
customthe solvent removed in vacuo
customThe residue was chromatographed
washeluted with a gradient of 0-10% EtOAc/CH2Cl2
concentrationconcentrated on the rotary evaporator

Quellen und Nachweise

ORD-Eintrag: ord-6245e0afc08d43e5a1d79d59a358a21a
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07781454B2

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