Lithium Hydroxide → 7-(trifluoromethyl)-1H-indazole-5-carboxylic acid

HRID 711079Notes

Reaction equation

HRID 711079 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:12]([O:14]C)=[O:13])[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[CH:8]2.[OH-].[Li+]>CO.O1CCCC1>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[CH:8]2

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67491553Methyl 7-(trifluoromethyl)-1H-indazole-5-carboxylate

Product 1

HCID 674918107-(trifluoromethyl)-1H-indazole-5-carboxylic acidYield 29.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 7-(trifluoromethyl)-1H-indazole-5-carboxylate (62 mg, 0.25 mmol) in methanol (2 mL) and tetrahydrofuran (2 mL) was added 1 N aqueous lithium hydroxide (0.76 mL, 0.76 mmol). The reaction was heated to 60° C. for 17 hours. The reaction was concentrated and the residue was diluted with water and acidified to pH=3 with 1 N aqueous hydrochloric acid. The solution was extracted with dichloromethane (3×). The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated to give the title compound (17 mg, 29%) as an off-white powder. +ESI (M+H) 231.1.

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe residue was diluted with water
  3. extractionThe solution was extracted with dichloromethane (3×)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d83e59d6c66f4a33aed33806310484af
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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