1,2-Dibromoethane → Dibenzyl-[2,4-difluoro-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-amine

HRID 38107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38107
[CH2:1]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:9]1[C:10]([F:28])=[C:11]([C:16]2[C:17]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[C:18]([SH:21])[NH:19][N:20]=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+].Br[CH2:43][CH2:44]Br>CN(C=O)C>[CH2:29]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]2[C:17]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[C:18]3[S:21][CH2:43][CH2:44][N:19]3[N:20]=2)[C:10]=1[F:28])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

5

Edukt 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178505870HCID 178505870, Verbindung

Produkt 1

HCID 58477092Dibenzyl-[2,4-difluoro-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-amineAusbeute 40,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-(3-Dibenzylamino-2,6-difluoro-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol (1.26 g, 2.6 mmol) was dissolved in dry DMF (33 mL) under nitrogen atmosphere. Solid potassium carbonate (1.8 g, 13 mmol, 5 eq) was added followed by 1,2-dibromoethane (0.252 mL, 2.86 mmol, 1.1 eq) and the suspension was stirred at room temperature for 4 hours. DMF was then removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate. The organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness. 537 mg of dibenzyl-[2,4-difluoro-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-amine were obtained as white solid (47% over 2 steps).

Aufarbeitung

  1. customDMF was then removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2cecd265eb72433db66bed924129f72c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524707B2

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