Lithium Hydroxide → 3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid

HRID 530838Notes

Reaction equation

HRID 530838 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19]CC)=[O:18])[CH:15]=3)[N:10]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[Li+].[OH-]>C1COCC1>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=3)[N:10]([C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67984978ethyl 3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylate

Product 1

HCID 679849753-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of ethyl 3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylate (260 mg, 0.5 mmol) in THF (5 mL) was added LiOH (1M, 2 mL). The reaction mixture was stirred at room temperature for overnight. HCL was added to adjust the pH to 4-5 and ethyl acetated was added. The extract was washed with water (10 mL0 and dry over sodium sulfate and concentrated to give the desired product in 95% yield.

Workup

  1. additionHCL was added
  2. additionacetated was added
  3. washThe extract was washed with water (10 mL0
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-590d07430c904bf8a5e6146d542f6edf
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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