Hexane → methyl 1H-indazole-3-carboxylate

HRID 1372737Notes

Reaction equation

HRID 1372737 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[N:2]1.[CH3:13][Si](C=[N+]=[N-])(C)C.CCCCCC>C1COCC1.CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1

Participants

6

Reactant 3

HCID 8058HexaneHCID 78250Indazole-3-carboxylic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 657476methyl 1H-indazole-3-carboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Indazole-3-carboxylic acid (5.00 g, 30.8 mmol) was dissolved in THF (200 ml) and methanol (15 ml). To the resulting solution was added (trimethylsilyl)diazomethane (a 2.0M n-hexane solution, 20 ml, 40.1 mmol) under stirring at 0° C. After stirring at room temperature for 3 hours, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was crystallized by the addition of n-hexane, and the crystals thus obtained were collected by filtration and dried under reduced pressure to give methyl indazole-3-carboxylate (3.71 g, 68%) as a colorless solid.

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. distillationthe reaction mixture was distilled under reduced pressure
  3. customto remove the solvent
  4. customThe residue was crystallized by the addition of n-hexane
  5. customthe crystals thus obtained
  6. filtrationwere collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-79b2559f72c046a98a1914b3180006ff
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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