Toluene → HCID 178520024, compound

HRID 1749869Notes

Reaction equation

HRID 1749869 reaction equation
[Br: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.C1(C)C=CC=CC=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Br: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 4

HCID 1140TolueneHCID 24436Sodium SulfateHCID 12689298Methyl 5-bromo-1H-indazole-3-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 178520024HCID 178520024, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of methyl 5-bromo-1H-indazole-3-carboxylate (2.21 g, 8.66 mmol) in THF (60 mL) was cooled to −10° C., and added dropwise with a 1 M solution of diisobutylaluminum hydride in toluene (36.0 mL, 36.0 mmol). 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 filtered through Celite. The filtrate was concentrated, and the resulting solid was suspended in methylene chloride and thereby washed to obtain (5-bromo-1H-indazol-3-yl)methanol (0.712 g, 36%).

Workup

  1. additionAfter completion of the addition
  2. stirringstirred overnight at room temperature
  3. customto terminate
  4. customthe reaction
  5. filtrationfiltered through Celite
  6. concentrationThe filtrate was concentrated
  7. washwashed

Sources & evidence

ORD record
ord-8cb01f961f884fce924a3c5aaf4275c3
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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