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Hydrazine → 3-(3,5-Dimethyl-1H-pyrazol-4-ylmethyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester

HRID 1754703
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1754703
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([CH2:17][CH:18]([C:22](=O)[CH3:23])[C:19](=O)[CH3:20])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:25][NH2:26]>CO.ClCCl>[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([CH2:17][C:18]2[C:22]([CH3:23])=[N:25][NH:26][C:19]=2[CH3:20])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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Komponenten

5

Edukt 2

HCID 9321HydrazineHCID 59593276HCID 59593276, Verbindung

Produkt 1

HCID 595933443-(3,5-Dimethyl-1H-pyrazol-4-ylmethyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 3-(2-acetyl-3-oxo-butyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (513, 1.20 g, 3.63 mmol) in methanol (15.0 mL), cooled to −20° C. under an atmosphere of nitrogen, was added hydrazine (0.128 g, 4.00 mmol) in dichloromethane (6.0 mL). The reaction was stirred for 2 hours. The reaction was concentrated to remove the solvents, and the residue was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 60% ethyl acetate in hexane to give a white solid (514, 1.0 g, 84.4%). MS (ESI) [M+H+]+=327.4.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customto remove the solvents
  3. additionthe residue was poured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel column chromatography
  9. washeluting with 60% ethyl acetate in hexane
  10. customto give a white solid (514, 1.0 g, 84.4%)

Quellen und Nachweise

ORD-Eintrag
ord-302962f5a4dc45c39bf9ce67c04b0912
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09169250B2

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