Water → 3-Bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine

HRID 570140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570140
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:11]3[N:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl>[Br:17][C:16]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][N:10]2[CH:15]=[CH:14][CH:13]=[N:12][C:11]=12

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 692972612-(4-Fluorophenyl)pyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 837474383-Bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidineAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine (5.8 g, 0.027 mol) in chloroform (60 mL) is added, at 0° C., N-bromosuccinimide (4.8 g, 0.027 mol). The mixture is stirred at room temperature for 1 h 30. The reaction mixture is then poured into water and extracted with dichloromethane (3×100 mL). The organic layer is dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material is filtered through a short pad of silica. 6 g (75%) of 3-bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine are obtained as a brown solid which is used in the next step without further purification.

Aufarbeitung

  1. extractionextracted with dichloromethane (3×100 mL)
  2. dry with materialThe organic layer is dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe crude material is filtered through a short pad of silica

Quellen und Nachweise

ORD-Eintrag
ord-283af891170a41819dfe6340dae04fa3
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023844B2

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