Sodium Hydroxide → 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid

HRID 1501711Notes

Reaction equation

HRID 1501711 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:16]([O:18]C)=[O:17])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:9]=2[CH:10]=1.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:16]([OH:18])=[O:17])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67468180Methyl 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylate

Product 1

HCID 674684486-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylate (3 g, 9.28 mmol) in ethanol (30 mL), aqueous NaOH solution (0.56 g in 3 mL water, 13.93 mmol) was added and reaction stirred at 60° C. for 4 h. On completion, ethanol was removed under reduced pressure and residue acidified with 1N HCl to pH 6. The resulting precipitate was filtered, washed with water and dried to 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid (2.3 g, 80.4%).

Workup

  1. customreaction
  2. customOn completion, ethanol was removed under reduced pressure and residue
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. dry with materialdried to 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid (2.3 g, 80.4%)

Sources & evidence

ORD record
ord-71fa240c0cb4435fa5f5a929d62616b7
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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