Cesium carbonate → Ethyl {[5-(4-chlorophenyl)-3-cyano-6-(2,4-dichlorophenyl)pyridin-2-yl]oxy}acetate

HRID 8785

Reaktionsgleichung

[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(OCC)(=O)CO.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[C:10]([C:2]#[N:1])[C:5]([O:4][CH2:3][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:6][C:7]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:16][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A solution of 1.55 g (3.93 mmol) of the product from Step A in toluene (20 mL) was treated with ethyl glycolate (0.41 mL; 4.33 mmol) and cesium carbonate (2.54 g; 7.8 mmol). The reaction mixture was heated in a sealed pressure tube at 80° C. and stirred for 6 h. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 460.9 (M+1), 462.9 (M+3); Rt=4.50 min.

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
custompartitioned between ethyl acetate and saturated NaHCO3 solution
washThe organic layer was washed twice with saturated NaHCO3 solution, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient)

Quellen und Nachweise

ORD-Eintrag: ord-1e05681d149548b4b3f14d7ef43684ef
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091216B2

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