Sodium Bicarbonate → 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxylic acid

HRID 1037562Notes

Reaction equation

HRID 1037562 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:18](N)=[O:19].C(=O)(O)[O-:22].[Na+]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:18]([OH:19])=[O:22]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 677763456-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxamide

Product 1

HCID 675127396-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxylic acidYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A stirred suspension of compound (xv) in conc. sulfuric acid (5 mL) and water (5 mL) were heated to 90° C. After 2 h the reaction mixture was diluted with water, neutralized with sodium bicarbonate and extracted with EtOAc (3×15 mL). The organic layer was dried (Na2SO4) and concentrated to give 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carboxylic acid (xvi) (70 mg, 35%) as a white solid. ESI-MS m/z calculated for [M+H]+: 336.98; found: 336.80.

Workup

  1. extractionextracted with EtOAc (3×15 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-640b76f069e5438c8a4e1fca0ee75a37
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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