2-Bromopropane → HCID 21252897, compound

HRID 1530828Notes

Reaction equation

HRID 1530828 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][O:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][N:8]=1)=[O:6].[CH:17](Br)([CH3:19])[CH3:18].[OH-].[K+]>COCCOC>[CH3:1][CH:2]([CH3:16])[CH2:3][O:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH:17]([CH3:19])[CH3:18])[N:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 14797Potassium HydroxideHCID 21252886HCID 21252886, compound

Product 1

HCID 21252897HCID 21252897, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 2-methylpropyl-1H-3-indazolecarboxylate (50 g; 0.24 moles) in 1,2-dimethoxy-ethane (300 ml) a solution of isopropyl bromide (27.5 ml; 0.29 moles) in 1,2-dimethoxy-ethane (100 ml) and KOH (13.5 g; 0.24 moles) was added and the mixture was heated under reflux for 8 hours. After removal of the solvent, the residue was dissolved in toluene (300 ml), the thus obtained solution was washed with 1N NaOH (100 ml), H2O (2×100 ml) and then dried and concentrated in vacuum. The residue was purified from the isomer 2-methylpropyl-2-isopropyl-2H-3-indazolecarboxylate via flash chromatography (eluent, hexane:ethyl acetate=95:5) to give the title compound (23 g) as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. customAfter removal of the solvent
  4. dissolutionthe residue was dissolved in toluene (300 ml)
  5. washthe thus obtained solution was washed with 1N NaOH (100 ml), H2O (2×100 ml)
  6. customdried
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified from the isomer 2-methylpropyl-2-isopropyl-2H-3-indazolecarboxylate via flash chromatography (eluent, hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-c5ce4c89a8334ce7b61165994e309aee
Source dataset
uspto-grants-2001_03
Patent number
US06197769B1

Reaction notes

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