2-Bromo-2',4'-difluoroacetophenone → HCID 24889415, Verbindung

HRID 255051

Reaktionsgleichung

Reaktionsgleichung von HRID 255051
[CH2:1]1[CH:8]2[C:4]3([C:10]([NH:12][C:13]([NH:15][CH2:16][CH2:17][O:18][CH3:19])=[S:14])=[O:11])[CH2:5][CH:6]([CH2:9][CH:2]1[CH2:3]3)[CH2:7]2.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31])=[O:23]>C(O)C>[C:17]([O-:18])(=[O:23])[CH3:16].[NH4+:12].[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[C:22]1[N:15]([CH2:16][CH2:17][O:18][CH3:19])[C:13](=[N:12][C:10]([C:4]23[CH2:5][CH:6]4[CH2:9][CH:2]([CH2:1][CH:8]2[CH2:7]4)[CH2:3]3)=[O:11])[S:14][CH:21]=1

Komponenten

5

Edukt 2

HCID 27741852-Bromo-2',4'-difluoroacetophenoneHCID 86652458HCID 86652458, Verbindung

Produkt 2

HCID 517165Ammonium AcetateHCID 24889415HCID 24889415, VerbindungAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of example 14B (0.21 g, 0.75 mmol) in ethanol (10 mL) was added 2-bromo-1-(2,4-difluorophenyl)ethanone (0.18 g, 0.75 mmol). The mixture was heated to reflux for 3 hours and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with 1 M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. Purification by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile:ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/minutes provided 65 mg (20%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.47-1.64 (m, 4 H), 1.68-1.84 (m, 4 H), 2.05-2.20 (m, J=11.5 Hz, 2 H), 2.27 (s, 2 H), 2.58 (t, J=6.6 Hz, 1 H), 3.03 (s, 3 H), 3.52 (t, J=5.6 Hz, 2 H), 4.07 (t, J=5.4 Hz, 2 H), 6.99 (s, 1 H), 7.18-7.34 (m, 1 H), 7.48 (td, J=9.7, 2.5 Hz, 1 H), 7.60 (td, J=8.6, 6.6 Hz, 1 H); MS (ESI+) m/z 419 (M+H)+; Anal. Calculated for C22H24F2N2O2S: C, 63.14; H, 5.78; N, 6.69. Found: C, 63.18; H, 5.80; N, 6.72.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1 M aqueous NaHCO3
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size)

Quellen und Nachweise

ORD-Eintrag
ord-cf9ac6ed002f42d085eac15de353037a
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875639B2

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