Diazomethane → Methyl 1H-indazole-5-carboxylate

HRID 503116Notes

Reaction equation

HRID 503116 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[N+](=[CH2:15])=[N-]>O1CCCC1.C(OCC)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:15])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 42484541H-Indazole-5-carboxylic acid

Product 1

HCID 22260640Methyl 1H-indazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, to a solution of 910 mg of 1H-5-indazolecarboxylic acid in 60 ml tetrahydrofuran was added an excess amount of a solution of diazomethane in diethyl ether, and the mixture was stirred at the same temperature for 1 hour. After removing the solvent by distillation, the residue was added with 50 ml of ethyl acetate, sequentially washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 923 mg of the title compound as pale yellow crystals.

Workup

  1. customAfter removing the solvent
  2. distillationby distillation
  3. additionthe residue was added with 50 ml of ethyl acetate
  4. washsequentially washed with saturated aqueous sodium hydrogencarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6b9720a4cc154748aff7d0dfd6feea24
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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