Toluene → HCID 90308823, compound

HRID 2283684Notes

Reaction equation

HRID 2283684 reaction equation
C1(C)C=CC=CC=1.[C:8](OC(=O)C)([CH3:11])([CH3:10])[CH3:9].CS(O)(=O)=O.[Br:21][C:22]1[CH:23]=[C:24]2[C:28](=[C:29]([CH3:31])[CH:30]=1)[NH:27][N:26]=[CH:25]2>O>[Br:21][C:22]1[CH:30]=[C:29]([CH3:31])[C:28]2[C:24](=[CH:25][N:26]([C:8]([CH3:9])([CH3:10])[CH3:11])[N:27]=2)[CH:23]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6395Methanesulfonic AcidHCID 10908tert-Butyl acetateHCID 13820335-Bromo-7-methyl-1H-indazole

Product 1

HCID 90308823HCID 90308823, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Toluene (150 mL), acetic acid tert-butyl ester (360 mL), and methanesulfonic acid (22 mL) were added to 5-bromo-7-methyl-1H-indazole (35.9 g), and the reaction solution was stirred at 80° C. for 28 hours. The reaction solution was cooled to room temperature, water (500 mL) was added, and extracted with toluene (500 mL) and 200 mL toluene. After separation, the organic layer was washed with water twice. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. Hexane was added to the resultant residue and the insolubles were separated by filtration. The solvent was evaporated from the filtrate under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 5-bromo-2-(tert-butyl)-7-methyl-2H-indazole as a light red oily substance.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with toluene (500 mL) and 200 mL toluene
  3. customAfter separation
  4. washthe organic layer was washed with water twice
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated under vacuum
  7. additionHexane was added to the resultant residue
  8. customthe insolubles were separated by filtration
  9. customThe solvent was evaporated from the filtrate under vacuum
  10. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d0adf413ab00461ab9fb857c7c00ecec
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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