Sodium Hydroxide → 6-bromo-1-isopropyl-3-methyl-1H-indazole-4-carboxylic acid

HRID 1476447Notes

Reaction equation

HRID 1476447 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:15]([O:17]C)=[O:16])[C:5]2[C:6]([CH3:14])=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=[O:16])[C:5]2[C:6]([CH3:14])=[N:7][N:8]([CH:11]([CH3:12])[CH3:13])[C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67466747Methyl 6-bromo-1-isopropyl-3-methyl-1H-indazole-4-carboxylate

Product 1

HCID 674671276-bromo-1-isopropyl-3-methyl-1H-indazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 6-bromo-1-isopropyl-3-methyl-1H-indazole-4-carboxylate (7.5 g, 24.11 mmol) in ethanol (400 mL) was added sodium hydroxide (1.45 g, 36.17 mmol) in water (60 mL) and the reaction mixture was stirred at reflux for 6 h. The reaction mixture was concentrated under reduced pressure and the residue was diluted with water (150 mL), and acidified with 2N HCl to pH˜2. The precipitated acid was collected by filtration, washed with ether (200 mL, and dried to afford 6-bromo-1-isopropyl-3-methyl-1H-indazole-4-carboxylic acid as an off white solid (6.85 g, 95.6%). LCMS (ES−): 294.9 [M−H].

Workup

  1. temperatureat reflux for 6 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with water (150 mL)
  4. filtrationThe precipitated acid was collected by filtration
  5. washwashed with ether (200 mL
  6. customdried

Sources & evidence

ORD record
ord-1cb42a786981455fa642daab8fd81dde
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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