Hydrochloric Acid → 5-Bromo-6-fluoro-1H-indazole

HRID 1914772Notes

Reaction equation

HRID 1914772 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7](C(=O)C)[N:6]=[CH:5]2.Cl.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 596944751-(5-bromo-6-fluoro-1H-indazol-1-yl)ethanone

Product 1

HCID 468639235-Bromo-6-fluoro-1H-indazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1-(5-bromo-6-fluoro-1H-indazol-1-yl)ethanone (24C, 5.0 g, 19.5 mmol) was treated with aq HCl (3M soln., 100 mL) and methanol (20 mL) and heated at 90° C. for 3 h, when the reaction turns homogenous. The reaction mixture was cooled to room temperature and basified with aq. NaOH. A colorless solid precipitated out which was filtered and dried to yield 5-bromo-6-fluoro-1H-indazole (24D)

Workup

  1. customA colorless solid precipitated out which
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-6ed8b4a2edd64cc7b412005bb9f893a5
Source dataset
uspto-grants-2013_12
Patent number
US08614229B2

Reaction notes

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