Isoamyl nitrate → Methyl 4-iodo-1H-indazole-6-carboxylate

HRID 446223Notes

Reaction equation

HRID 446223 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([I:10])[C:7]([CH3:11])=[C:6]([NH2:12])[CH:5]=1.[N+:14]([O-])(OCCC(C)C)=O>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7]([CH:11]=[N:14][NH:12]2)=[C:8]([I:10])[CH:9]=1)=[O:13]

Participants

4

Reactant 2

HCID 10985Isoamyl nitrateHCID 67512060HCID 67512060, compound

Product 1

HCID 24728119Methyl 4-iodo-1H-indazole-6-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-amino-5-iodo-4-methyl-benzoic acid methyl ester (1.22 g, 4.21 mmol) in acetic acid (20 mL) was added isoamyl nitrate (0.675 mL, 4.63 mmol). The mixture was stirred at room temperature for 30 minutes and then concentrated under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give 1.15 g (91%) of 4-iodo-1H-indazole-6-carboxylic acid methyl ester, MS (M+H)=303.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-824a63379c384db098235b1a90a3e7c4
Source dataset
uspto-grants-2013_07
Patent number
US08476457B2

Reaction notes

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