Sodium Sulfate → HCID 178520030, compound

HRID 1749866Notes

Reaction equation

HRID 1749866 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11](OC)=[O:12].[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH2:11][OH:12]

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 126893691H-Indazole-3-carboxylic acid, 5-chloro-, methyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 178520030HCID 178520030, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of methyl 5-chloro-1H-indazole-3-carboxylate (2.11 g, 10.0 mmol) in THF (70 mL) was cooled to −10° C., and added dropwise with a 1 M solution of diisobutylaluminum hydride in toluene (36.0 mL). After completion of the addition, the mixture was stirred at −10° C. for 1 hour, and then stirred overnight at room temperature. The reaction mixture was added dropwise with saturated aqueous sodium sulfate under ice cooling to terminate the reaction, and then the reaction mixture was filtered through Celite. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain the objective (5-chloro-1H-indazol-3-yl)methanol (0.210 g, 11%).

Workup

  1. additionAfter completion of the addition
  2. stirringstirred overnight at room temperature
  3. customto terminate
  4. customthe reaction
  5. filtrationthe reaction mixture was filtered through Celite
  6. concentrationThe filtrate was concentrated
  7. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-d344d4ba0c7b4833887fada68078ac40
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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