N,N-Dimethylglycine hydrochloride → ethyl(E)-3-(3-methoxy-4-{5-[2-(4-trifluoromethylphenyl)vinyl]pyridin-2-yloxy}phenyl)propionate

HRID 884121

Reaktionsgleichung

Reaktionsgleichung von HRID 884121
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[O:22][CH3:23])=[N:6][CH:7]=1.[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[CH2:31])=[CH:28][CH:27]=1.Cl.CN(C)CC(O)=O.C([O-])(=O)C.[Na+]>C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.C(OCC)(=O)C.CN1CCCC1=O>[CH3:23][O:22][C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[CH:4]=[CH:3][C:2](/[CH:31]=[CH:30]/[C:29]2[CH:28]=[CH:27][C:26]([C:25]([F:24])([F:34])[F:35])=[CH:33][CH:32]=2)=[CH:7][N:6]=1

Komponenten

8

Edukt 4

HCID 75605N,N-Dimethylglycine hydrochlorideHCID 517045Sodium AcetateHCID 27827981-Ethenyl-4-(trifluoromethyl)benzeneHCID 68525811Ethyl 3-[4-(5-bromopyridin-2-yloxy)-3-methoxyphenyl]propionate

Produkt 1

HCID 68527484ethyl(E)-3-(3-methoxy-4-{5-[2-(4-trifluoromethylphenyl)vinyl]pyridin-2-yloxy}phenyl)propionate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 498840Bis(benzonitrile)palladium chlorideKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To ethyl 3-[4-(5-bromopyridin-2-yloxy)-3-methoxyphenyl]propionate (610 mg, 1.6 mmol) were added 4-trifluoromethylstyrene (0.332 mL, 2.2 mmol), dichlorobis(benzonitrile)palladium(II) (33 mg, 0.082 mmol), N,N-dimethylglycine hydrochloride (17 mg, 0.16 mmol), sodium acetate (263 mg, 3.2 mmol) and N-methylpyrrolidone (5 mL) under an argon atmosphere. The resulting solution was stirred under an argon atmosphere for 17 hours at 130° C. To the reaction solution was added ethyl acetate and filtered. The filtrate was washed with water, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), to thereby yield 500 mg of the title compound.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filtrate was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-f82192e12f3640d09f1283cea18172f6
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236826B2

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