Water → HCID 59334589, compound

HRID 1639790Notes

Reaction equation

HRID 1639790 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[C:12](OC)=[O:13].[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1.CCCCCC>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[CH2:12][OH:13]

Participants

6

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 59334499HCID 59334499, compound

Product 1

HCID 59334589HCID 59334589, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of methyl 5-chloro-2-methyl-2H-indazole-4-carboxylate (3.00 g, 13.4 mmol) in tetrahydrofuran (129 mL) was slowly added a solution (1 M, 40.1 mL, 40.1 mmol) of diisobutylaluminum hydride in hexane at −78° C., and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/2) to give the title compound (2.63 g, yield 99%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-8644406c633240ac87a5daeca041405a
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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