Triethylamine → 4-[(1E)-3-Oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzoic acid

HRID 2371061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371061
[F:1][C:2]([F:20])([F:19])[CH:3]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.I[C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[C:24]([C:31]([F:34])([F:33])[F:32])[CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[O:18]=[C:15]([NH:14][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:12])([F:13])[F:11])[CH:5]=1)[C:2]([F:19])([F:20])[F:1])/[CH:16]=[CH:17]/[C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[C:24]([C:31]([F:32])([F:34])[F:33])[CH:23]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 177333644-Iodo-2-(trifluoromethyl)benzoic acidHCID 86653067N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-acrylamide

Produkt 1

HCID 866530664-[(1E)-3-Oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under argon, first 3.34 g (7.90 mmol) of N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-acrylamide from Example 2. Stage 1, and then 2.49 g (7.90 mmol) of 4-iodo-2-(trifluoromethyl)benzoic acid (commercially available, CAS Registry Number: 954815-11-3), 0.206 g (7.90 mmol) of triphenylphosphine, 88.4 mg (0.39 nmol) of palladium(II) acetate and 13.5 g (133 mmol) of triethylamine were initially charged in 67 ml of N,N-dimethylformamide, and the reaction mixture was stirred at 100° C., for 5 hours. After addition of water, the solution was extracted with ethyl acetate, and then the organic phase was washed three times with saturated sodium chloride solution and dried over sodium sulphate. The solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel with ethyl acetate.

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate
  2. washthe organic phase was washed three times with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was chromatographed on silica gel with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-02c9469d2fc941ac8a1b156a84de9720
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710242B2

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