Methanol → Methyl 5-bromo-1H-indazole-3-carboxylate

HRID 2367694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367694
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]([OH:18])=[O:17].[CH3:19]O>>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]([O:18][CH3:19])=[O:17]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 71573585-bromo-1H-indazole-3-carboxylic Acid

Produkt 1

HCID 12689298Methyl 5-bromo-1H-indazole-3-carboxylateAusbeute 98 %

Versuchsvorschrift

Concentrated sulfuric acid (1 mL) was added to a suspension of 5-bromo-1H-indazole-3-carboxylic acid (CXV) (1.30 g, 5.39 mmol) in dry MeOH (50 mL) and heated to reflux for 4 h under argon. The solution was cooled to room temperature and the MeOH was evaporated under vacuum. The residue was dissolved in EtOAc and washed with water. The organic phase was dried over Na2SO4, filtered and concentrated to afford methyl 5-bromo-1H-indazole-3-carboxylate (CXVI) as a white solid (1.35 g, 5.29 mmol, 98% yield). 1H NMR (DMSO-d6) δ ppm 14.13 (s, 1H), 8.21 (d, J=1.6 Hz, 1H), 7.67 (d, J=7.2 Hz, 1H), 7.59 (dd, J=7.2, 1.2 Hz, 1H), 3.92 (s, 3H); ESIMS found for C9H7BrN2O2 m/z 256.0 (M+H).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 4 h under argon
  3. customthe MeOH was evaporated under vacuum
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-94b742b432644fb89b2567024364bb95
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697887B2

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