Lithium hydroxide, monohydrate → 6-bromo-1-ethyl-1H-indazole-4-carboxylic acid

HRID 85455Notes

Reaction equation

HRID 85455 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[N:8][N:9]([CH2:15][CH3:16])[C:10]=2[CH:11]=[C:12]([Br:14])[CH:13]=1)=[O:4].O[Li].O>C1COCC1.O>[Br:14][C:12]1[CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]2[CH:7]=[N:8][N:9]([CH2:15][CH3:16])[C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67466727HCID 67466727, compound

Product 1

HCID 674648836-bromo-1-ethyl-1H-indazole-4-carboxylic acidYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-bromo-1-ethyl-1H-indazole-4-carboxylic acid methyl ester (700 mg, 2.47 mmol) in THF (35 mL) was added a solution of LiOH.H2O (312 mg, 7.42 mmol) in water (15 mL) and the mixture was stirred at RT for 4 h. The reaction mixture was concentrated under reduced pressure, diluted with water (30 mL) and washed with EtOAc (2×25 mL). The aqueous layer was acidified (pH ˜5) with 1N HCl. The precipitated solid was collected by filtration and dried to furnish 6-bromo-1-ethyl-1H-indazole-4-carboxylic acid as a white solid (450 mg, 68%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water (30 mL)
  3. washwashed with EtOAc (2×25 mL)
  4. filtrationThe precipitated solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-c4040efa5f8f4d4aafe7a8904a9d6c1d
Source dataset
uspto-grants-2014_09
Patent number
US08846935B2

Reaction notes

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