5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide → 5-Iodo-1H-indazole-3-carbaldehyde

HRID 218461

Reaction equation

HRID 218461 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11](N(OC)C)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH:11]=[O:12]

Participants

4

Reactant 2

HCID 205807385-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 1785200355-Iodo-1H-indazole-3-carbaldehydeYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide (500 mg, 1.51 mmol), from Synthetic Preparation 6, in THF (10 mL) at 0° C. was added lithium aluminum hydride (61 mg, 1.66 mmol). After 30 min, the reaction was quenched by the slow addition of EtOAc followed by 0.4N NaHSO4, and extracted. The organic layer was washed with brine, dried, and concentrated. The crude product was purified by flash chromatography to give 5-iodo-1H-indazole-3-carboxaldehyde (240 mg, 58.2%).

Workup

  1. customthe reaction was quenched by the slow addition of EtOAc
  2. extractionextracted
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-5fc2b1c1673d47bf8439ad9dccac66dc
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Linked notes

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