1,2-Dichloroethane → HCID 18373180, Verbindung

HRID 842378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842378
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[C:14]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH2:30])[CH:28]=2)[CH:23]=[N:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(Cl)CCl>CN(C=O)C>[C:14]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH:30][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[C:3]=3[N+:11]([O-:13])=[O:12])[CH:28]=2)[CH:23]=[N:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Komponenten

5

Edukt 3

HCID 111,2-DichloroethaneHCID 215753-Methyl-2-nitrobenzoic acidHCID 120186071-BOC-6-AMINO-INDAZOLE

Produkt 1

HCID 18373180HCID 18373180, VerbindungAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirring solution of 3-methyl-2-nitrobenzoic acid (1.8 g, 10.1 mmol) and 1-Boc-6-amino-indazole (2.37 g, 10.1 mmol) in DMF (20 mL) was added EDC (3.17 g, 15.2 mmol). After stirring for 16 h, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and 1 M citric acid. The layers were separated and the organic phase was washed again with 1 M citric acid, once with water, twice with satd aq NaHCO3, and once with brine. The organic phase was then dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in a minimal volume of chloroform and chromatographed over silica gel, eluting with a gradient of 40% ethyl acetate/hexanes through 70% ethyl acetate/hexanes. The product containing fractions were combined and concentrated in vacuo to give 2.34 g (58%) of off-white solid.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and 1 M citric acid
  3. customThe layers were separated
  4. washthe organic phase was washed again with 1 M citric acid, once with water, twice with satd aq NaHCO3
  5. dry with materialThe organic phase was then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in a minimal volume of chloroform
  9. customchromatographed over silica gel
  10. washeluting with a gradient of 40% ethyl acetate/hexanes through 70% ethyl acetate/hexanes
  11. additionThe product containing fractions
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-caf86d0a7bfa4abba8c263de13806d30
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372759B1

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