Hydrochloric Acid → 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylic acid

HRID 2367696Notes

Reaction equation

HRID 2367696 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[N:8]=[C:7]2[C:19]([O:21]C)=[O:20].Cl>O>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[N:8]=[C:7]2[C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69803802HCID 69803802, compound

Product 1

HCID 698056555-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2 N Aqueous NaOH solution (10 mL) was added to a suspension of methyl 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylate (CXVII) (1.30 g, 3.83 mmol) in water (20 mL) and heated at 90° C. for 1 h. The solution was cooled to room temperature, diluted with ice water and acidified to pH 3.0 with 10% aqueous HCl. The solids formed were filtered, washed with cold water and dried under vacuum at room temperature to get 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carboxylic acid (CXVIII) as a white solid (0.87 g, 2.68 mmol, 70% yield). ESIMS found for C13H13BrN2O3 m/z 326.0 (M+H).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed with cold water
  5. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-151ec9061b974ba2adf1142f8ff90425
Source dataset
uspto-grants-2014_04
Patent number
US08697887B2

Reaction notes

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