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

HRID 218478

Reaktionsgleichung

Reaktionsgleichung von HRID 218478
[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]

Komponenten

7

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ad5e6f2faee44796820de143999deeae
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198456B2

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