5-Iodo-1H-indazole → 1H-Indazole-5-carboxaldehyde

HRID 218452

Reaction equation

HRID 218452 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH:11](O[Na])=[O:12].[C]=O>CN(C=O)C.[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([CH:11]=[O:12])=[CH:10][CH:9]=2)[CH:5]=[N:6]1

Participants

7

Reactant 3

HCID 218947395-Iodo-1H-indazoleHCID 178418416HCID 178418416, compoundHCID 178526064HCID 178526064, compound

Product 1

HCID 212506441H-Indazole-5-carboxaldehydeYield 59%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 5-iodoindazole (10 g, 41 mmol), HCOONa (5.57 g, 82 mmol) and PdCl2(PPh3)2 (1.44 g, 2.05 mmol) in DMF (60 mL) was put under vacuum and charged with carbon monoxide (CO). This process was repeated three times, after which the mixture was kept at 110° C. for 6 hr. After cooling to room temperature (rt), the reaction mixture was diluted with brine and extracted with EtOAc. The organic phases were combined, washed with brine, dried, and concentrated. The crude product was purified by column chromatography to afford 1H-indazole-5-carboxaldehyde (3.52 g, 59%) as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-409fa49f0ea84d03acfb949dd7ff02f8
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Linked notes

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