Water → 4-Bromo-3-methoxy-1H-indazole

HRID 1716731Notes

Reaction equation

HRID 1716731 reaction equation
C(OC([N:6]1[C:14]2[C:9](=[C:10]([Br:15])[CH:11]=[CH:12][CH:13]=2)[C:8]([O:16][CH3:17])=[N:7]1)=O)C.O.[Li+].[OH-]>C1COCC1>[Br:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[C:8]([O:16][CH3:17])=[N:7][NH:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59831716ethyl 4-bromo-3-methoxy-1H-indazole-1-carboxylate

Product 1

HCID 598317764-Bromo-3-methoxy-1H-indazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 4-Bromo-3-methoxy-indazole-1-carboxylic acid ethyl ester CLXXXV (1.27 g, 4.14 mmol) in THF (28 ml) and H2O (9 ml) was added LiOH (397 mg, 16.6 mmol). The reaction mixture was stirred at reflux for 2 hours then at room temperature for 15 hours. The mixture was concentrated. The residue was diluted with EtOAc (50 ml), washed with HCl (IM) and brine, dried over MgSO4, filtered and concentrated affording 4-Bromo-3-methoxy-1H-indazole CLXXXVI as an off-white solid (98% yield), which was used without further purification in the next step.

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe mixture was concentrated
  3. additionThe residue was diluted with EtOAc (50 ml)
  4. washwashed with HCl (IM) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-67b694fca8de484ca4981601b30e2895
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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