Boron tribromide → 1-Isobutyl-1H-indazol-5-ol

HRID 2112213Notes

Reaction equation

HRID 2112213 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14]C)=[CH:11][CH:12]=2)[CH:7]=[N:6]1)[CH:2]([CH3:4])[CH3:3].B(Br)(Br)Br>ClCCl>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:14])=[CH:11][CH:12]=2)[CH:7]=[N:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 574187691-Isobutyl-5-methoxy-1H-indazole

Product 1

HCID 574187701-Isobutyl-1H-indazol-5-olYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (-78° C.) solution of 1-isobutyl-5-methoxy-1H-indazole (2.57 g, 12.6 mmol) in dichloromethane (100 mL) was added BBr3 (25 mL of 1M solution in dichloromethane). The mixture was stirred at −78° C. for 2 hours and then warmed to room temperature and stirred for 18 hours. The reaction mixture was poured into ice water and extracted with dichloromethane. The organic extract was filtered and concentrated under reduced pressure to afford 2.3 g of solid (96% yield).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 18 hours
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. filtrationwas filtered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40dedee57f8044e9a2d5dea1046874bc
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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