Sodium Sulfate → (1H-indazol-5-yl)methanol

HRID 1854666Notes

Reaction equation

HRID 1854666 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](OC)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].C([Al+]CC(C)C)C(C)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][OH:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 24436Sodium Sulfate2×HCID 21225700DiisobutylaluminumhydrideHCID 22260640Methyl 1H-indazole-5-carboxylate

Product 1

HCID 1514190(1H-indazol-5-yl)methanolYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 1H-indazole-5-carboxylate (300 mg, 1.69 mmol, prepared according to the procedure described in JP-11-228513) in 8.5 mL of dry toluene was added diisobutylaluminum hydride (1 mol/L in n-hexane, 3.4 mL) under nitrogen at −78° C. After the reaction mixture was stirred at the same temperature for 3 h, saturated Na2SO4 aqueous solution was added carefully at 0° C. After the solution was stirred at room temperature, a sufficient amount of Na2SO4 was added with additional stirring for drying. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (chloroform/methanol=98/2 to 85/15) to obtain (1H-indazol-5-yl)methanol (125 mg, 50%).

Workup

  1. stirringAfter the solution was stirred at room temperature
  2. stirringwith additional stirring
  3. customfor drying
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (chloroform/methanol=98/2 to 85/15)

Sources & evidence

ORD record
ord-ffa202eda4674f96bbc27b5e60bd0f02
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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