Potassium Carbonate → methyl 6-amino-5-methyl-2H-indazole-7-carboxylate

HRID 245614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245614
[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:15])=[C:7](Br)[CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[CH:10]2)=[O:4].[C:16]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:15])=[C:7]([CH3:16])[CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[CH:10]2)=[O:4]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 57990193HCID 57990193, Verbindung

Produkt 1

HCID 57990198methyl 6-amino-5-methyl-2H-indazole-7-carboxylateAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

To a solution of 500 mg (1.85 mmol) of 6-amino-5-bromo-1H-indazole-7-carboxylic acid methyl ester, prepared as in step a in example 16, in 10 mL of dioxane under an atmosphere of argon is added 767 mg (5.55 mmol) of K2CO3, 106 mg (0.09 mmol) of tetrakis(triphenylphsophine)palladium and 232 mg (1.85 mmol) of trimethylboroxine. The reaction mixture is stirred in a microwave oven at 180° C. for 5 minutes. After filtration over Celite and concentration in vacuo, the residue is purified sequentially by flash chromatography (SiO2, hexanes/ethyl acetate 6:4) and reverse phase chromatography to afford 163 mg of product (43% over two steps) as a pale yellowish solid; LC/MS:206/207 (M+H)+.

Aufarbeitung

  1. filtrationAfter filtration
  2. concentrationover Celite and concentration in vacuo
  3. customthe residue is purified sequentially by flash chromatography (SiO2, hexanes/ethyl acetate 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-cd934c002a61467d8c2b57b6afe546f2
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658801B2

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