Sodium Bicarbonate → 3-bromo-2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

HRID 1787575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1787575
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8](C(O)=O)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.C(=O)(O)[O-].[Na+].[Br:23]NC(=O)CCC(N)=O>CN(C=O)C.O.C(OCC)(=O)C>[Br:23][C:8]1[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:11][N:10]2[CH2:12][CH2:13][CH2:14][C:9]=12

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 9834204N-BromosuccinamideHCID 597100292-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic Acid

Produkt 1

HCID 597100253-bromo-2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoleAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Stir a mixture of 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid (Preparation 2C; 2 g, 8.7 mmol), sodium bicarbonate (3.3 g, 38.4 mmol), and N-bromosuccinamide (1.7 g, 9.6 mmol) in DMF (50 mL) at room temperature for 2 h. Dilute the crude mixture with water (50 mL) and ethyl acetate (100 mL). Separate the ethyl acetate layer, extract with saturated sodium chloride solution, dry over anhydrous sodium sulfate, filter, and evaporate to a solid mass. Purify by MPLC (SiO2, 1:1 ethyl acetate/hexane) to obtain 1.62 g (70%) of the title compound as a cream solid. MS (ES) m/z 264 (M+H).

Aufarbeitung

  1. customSeparate the ethyl acetate layer
  2. extractionextract with saturated sodium chloride solution
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. customevaporate to a solid mass
  6. customPurify by MPLC (SiO2, 1:1 ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3e9fe18969784c3d98b1483d8da8d936
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511056B2

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