Methyl 5-bromo-1H-indazole-3-carboxylate → methyl 5-formyl-1H-indazole-3-carboxylate

HRID 218478

Reaction equation

HRID 218478 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](Br)[CH:12]=2)[NH:7][N:6]=1)=[O:4].[CH:15](O[Na])=[O:16]>CN(C=O)C.CCOC(C)=O.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>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:15]=[O:16])[CH:12]=2)[NH:7][N:6]=1)=[O:4]

Participants

7

Reactant 2

HCID 12689298Methyl 5-bromo-1H-indazole-3-carboxylateHCID 178526064HCID 178526064, compound

Product 1

HCID 24958745methyl 5-formyl-1H-indazole-3-carboxylateYield 54%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromo-1H-indazole-3-carboxylic acid methyl ester (1 g, 3.92 mmol), HCOONa (400 mg, 5.88 mmol), and PdCl2(PPh3)2 (138 mg, 0.2 mmol) in DMF (10 mL) was put under vacuum, and charged with CO. This process was repeated three times, and the mixture was kept at 110° C. for 6 hr. The reaction mixture was cooled to rt, diluted with EtOAc and water, and extracted. The organic phase was dried and concentrated. Purification via flash chromatography afforded 5-formyl-1H-indazole-3-carboxylic acid methyl ester (430 mg, 54%).

Workup

  1. additioncharged with CO
  2. extractionextracted
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customPurification via flash chromatography

Sources & evidence

ORD record
ord-ad5e6f2faee44796820de143999deeae
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Linked notes

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