Dibromomethane → 1-(3-Dibenzylamino-2,6-difluoro-phenyl)-2-[1,3]dithietan-2-ylidene-2-pyridin-4-yl-ethanone

HRID 38105

Reaktionsgleichung

Reaktionsgleichung von HRID 38105
[CH2:1]([N:8]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:9]1[C:10]([F:25])=[C:11]([C:16](=[O:24])[CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[C:12]([F:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:39](=[S:41])=[S:40].Br[CH2:43]Br>CS(C)=O.O>[CH2:26]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[C:10]([F:25])=[C:11]([C:16](=[O:24])[C:17](=[C:39]2[S:41][CH2:43][S:40]2)[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[C:12]([F:15])=[CH:13][CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

7

Edukt 4

HCID 3024DibromomethaneHCID 6348Carbon DisulfideHCID 11430Potassium CarbonateHCID 584771201-(3-Dibenzylamino-2,6-difluoro-phenyl)-2-pyridin-4-yl-ethanone

Produkt 1

HCID 584770931-(3-Dibenzylamino-2,6-difluoro-phenyl)-2-[1,3]dithietan-2-ylidene-2-pyridin-4-yl-ethanoneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-Dibenzylamino-2,6-difluoro-phenyl)-2-pyridin-4-yl-ethanone (2.14 g, 4.994 mmol) in dry DMSO (22 mL) under nitrogen atmosphere solid potassium carbonate (2.07 g, 15 mmol, 3 eq) was added at room temperature, followed by carbon disulfide (0.9 mL, 15 mmol, 3 eq) and dibromomethane (1.05 mL, 15 mmol, 3 eq). The reaction mixture was stirred at room temperature for 3 hour and then poured into stirred iced water (150 mL). The aqueous phase was extracted with ethyl acetate (3 x 70 mL) and the combined organic layers were washed with water, dried and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (n-hexane/ethyl acetate 7:3 to 6:4) to obtain 1.26 g of 1-(3-dibenzylamino-2,6-difluoro-phenyl)-2-[1,3]dithietan-2-ylidene-2-pyridin-4-yl-ethanone as yellow solid (49%).

Aufarbeitung

  1. additionpoured
  2. extractionThe aqueous phase was extracted with ethyl acetate (3 x 70 mL)
  3. washthe combined organic layers were washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography (n-hexane/ethyl acetate 7:3 to 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-17697ae026424e0b9282ea5373648abf
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524707B2

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