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

HRID 751261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751261
[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 3; 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 50 mL of water and 100 mL of ethyl acetate. Separate the ethyl acetate layer, extract with saturated brine, dry over anhydrous sodium sulfate, filter, and evaporate to a solid mass. Purify by MPLC (SiO2, 50% ethyl acetate-hexane) to obtain the title compound (1.62 g, 70%) as a cream solid. MS ES+ m/e 264 (M+1), MS ES+ m/e 266 (M+2).

Aufarbeitung

  1. customSeparate the ethyl acetate layer
  2. extractionextract with saturated brine
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. customevaporate to a solid mass
  6. customPurify by MPLC (SiO2, 50% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-baa6149b86a2430aacd631a80e97750f
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405299B2

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