Boron tribromide → 4-methyl-1H-indazol-5-ol

HRID 1269820

Reaktionsgleichung

Reaktionsgleichung von HRID 1269820
B(Br)(Br)Br.C[O:6][C:7]1[C:8]([CH3:16])=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[CH:10]2.C(=O)([O-])O.[Na+]>ClCCl>[CH3:16][C:8]1[C:7]([OH:6])=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[N:11][NH:12]2

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 229340895-methoxy-4-methyl-1H-indazole

Produkt 1

HCID 229335464-methyl-1H-indazol-5-olAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of boron tribromide (0.513 ml, 5.43 mmol) in dichloromethane (5 ml) was added dropwise to a solution of the 5-methoxy-4-methyl-1H-indazole (400 mg, 2.47 mmol) obtained in Example 401 in dichloromethane (5 ml) at 0° C. After 1 hour, the reaction solution was poured onto ice (50 ml), adjusted to pH 4 to 5 with a saturated aqueous sodium hydrogencarbonate solution, and then extracted with chloroform (20 ml×2) and ethyl acetate (20 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain 4-methyl-1H-indazol-5-ol (149 mg, 41%).

Aufarbeitung

  1. additionthe reaction solution was poured onto ice (50 ml)
  2. extractionextracted with chloroform (20 ml×2) and ethyl acetate (20 ml×2)
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe organic layer dried
  5. concentrationwas concentrated under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-98d5135a6b29442abfe07f34ab95a345
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199147B2

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