Ethyl Acrylate → 3-(4-Benzyloxycarbonylamino-2-fluoro-phenyl)-acrylic Acid Ethyl Ester

HRID 1163341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1163341
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[C:13]([F:18])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22].CCN(C(C)C)C(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:25]([O:24][C:20](=[O:23])[CH:21]=[CH:22][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:19])=[CH:12][C:13]=1[F:18])[CH3:26]

Komponenten

7

Edukt 4

HCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 67274244N-(4-bromo-3-fluorophenyl)carbamic acid phenylmethyl ester

Produkt 1

HCID 672740363-(4-Benzyloxycarbonylamino-2-fluoro-phenyl)-acrylic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A suspension of 9.72 g (4-bromo-3-fluoro-phenyl)-carbamic acid benzyl ester (30 mmol), 6 g ethyl acrylate (60 mmol), 10.2 ml DIPEA (60 mmol), 112 mg palladium acetate (3 mmol), and 1.57 g triphenylphosphine (6 mmol) in 10 ml DMF were stirred at 130° C. for 48 h. The reaction was monitored by TLC. The DMF was evaporated, the residue dissolved in dichloromethane, washed with water and brine, dried over Mg sulfate, filtered and the filtrate evaporated. The residue was purified by chromatography, using a 7/3 N-hexane/ethyl acetate mixture as eluent.

Aufarbeitung

  1. customThe DMF was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over Mg sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated
  7. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c1d27a6614b24fdda28a9b9d81e4992a
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820823B2

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