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

HRID 59802

Reaction equation

HRID 59802 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-70809c7613524ef497c67b64df382b7e
Source dataset
uspto-grants-2016_09
Patent number
US09440956B2

Linked notes

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