Methanol → methyl 7-ethyl-1H-indazole-5-carboxylate

HRID 1880407Notes

Reaction equation

HRID 1880407 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[CH:8]2)[CH3:2].OS(O)(=O)=O.[CH3:20]O>>[CH2:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:20])=[O:13])[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[CH:8]2)[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 552714657-ethyl-1H-indazole-5-carboxylic acid

Product 1

HCID 60144278methyl 7-ethyl-1H-indazole-5-carboxylateYield 47%

Procedure

To a solution of 7-ethyl-1H-indazole-5-carboxylic acid (500 mg, 2.63 mmol) in MeOH (15 mL) was added conc. H2SO4 (0.25 mL). The mixture was heated at reflux overnight. The solvent was removed under reduced pressure to afford a tan solid that was purified by flash chromatography (40 g column) using 15-30% EtOAc/heptane to afford methyl 7-ethyl-1H-indazole-5-carboxylate (252 mg, 47%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. customto afford a tan solid
  5. customthat was purified by flash chromatography (40 g column)

Sources & evidence

ORD record
ord-6386bd9dc3154cac8e199799417c73ef
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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