Sodium Hydroxide → 1-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid

HRID 59809Notes

Reaction equation

HRID 59809 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH:14]([CH3:16])[CH3:15])=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=2)[CH:6]=1)=[O:4].[OH-].[Na+]>CO>[CH:14]([N:11]1[C:12]2[C:8](=[C:7]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=3)[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:13]=2)[CH:9]=[N:10]1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 596277651-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid methyl ester

Product 1

HCID 596277631-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acidYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid methyl ester (0.5 g, 1.62 mmol) was dissolved in methanol (30 mL) and 2N aqueous NaOH (3 mL) was added. The reaction mixture was stirred at room temperature overnight, then partitioned between 1N aqueous HCl and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure to provide 0.48 g (100%) of 1-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid

Workup

  1. custompartitioned between 1N aqueous HCl and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e41ac3e20414e5c8817270de9303adb
Source dataset
uspto-grants-2016_09
Patent number
US09440956B2

Reaction notes

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