Hydrochloric Acid → 6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carboxylic acid

HRID 38853Notes

Reaction equation

HRID 38853 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:5]=[C:6]([C:23]([O:25]C)=[O:24])[C:7]2[CH:8]=[N:9][N:10]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:11]=2[CH:12]=1.Cl>O1CCCC1.O>[Br:3][C:4]1[CH:5]=[C:6]([C:23]([OH:25])=[O:24])[C:7]2[CH:8]=[N:9][N:10]([S:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)(=[O:15])=[O:14])[C:11]=2[CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66691545methyl 6-bromo-1-tosyl-1H-indazole-4-carboxylate

Product 1

HCID 666917216-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carboxylic acidYield 65.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.774 g, 32.3 mmol) was added to a stirred suspension of methyl 6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carboxylate (5.51 g, 13.46 mmol) in tetrahydrofuran (50 ml) and water (15 ml) and the reaction mixture was stirred at RT for 1 h. The reaction mixture was poured onto 2N HCl (800 ml) with stirring. The precipitate formed was filtered off under vacuum and dried at 50° C. in a vacuum oven for 18 h to give the title compound as a yellow solid (3.5 g).

Workup

  1. stirringwith stirring
  2. customThe precipitate formed
  3. filtrationwas filtered off under vacuum
  4. customdried at 50° C. in a vacuum oven for 18 h

Sources & evidence

ORD record
ord-ce676e9a5e544af7b3ac49545503a9cb
Source dataset
uspto-grants-2013_09
Patent number
US08524751B2

Reaction notes

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