Water → 5-Bromo-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-ol

HRID 2423104Notes

Reaction equation

HRID 2423104 reaction equation
[Br:1][C:2]1[C:3]([O:26]C)=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([O:17]CC3C=CC=CC=3)=[C:13]([F:25])[CH:12]=1)[N:6]=[CH:5]2.B(Br)(Br)Br.O.C(OCC)(=O)C>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:25])[CH:12]=3)[N:6]=[CH:5][C:4]=2[C:3]=1[OH:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 592729765-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-(methyloxy)-1H-indazole

Product 1

HCID 1359103655-Bromo-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-olYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-(methyloxy)-1H-indazole (D20) (71 mg) in dry dichloromethane (2 mL) was cooled to −78° C. under argon and treated dropwise with boron tribromide solution (0.75 mL of 1M solution in dichloromethane, 0.75 mmol). The mixture was allowed to reach room temperature and was stirred overnight. Water and ethyl acetate were added and the pH of the aqueous layer was adjusted to 7 and the product was extracted into ethyl acetate. The extracts were dried (Na2SO4), concentrated and chromatographed (silica gel, 0-100% ethyl acetate in hexane) to give the title compound (E11) as a beige solid (40 mg)

Workup

  1. customto reach room temperature
  2. extractionthe product was extracted into ethyl acetate
  3. dry with materialThe extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed (silica gel, 0-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4c8adedf33174b289b4e8c5b249e9ffd
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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