Reaktion #305641

Reaktionsgleichung

NaHSO3

iodine

N-methoxy-N-methyl-1H-indazole-3-carboxamide

bis(trifluoroacetoxy)iodobenzene

→

5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide

Ausbeute 72.0%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto precipitate
2. 2
   Filtrationwhich was then filtered
3. 3
   EinengenThe filtrate was concentrated
4. 4
   Sonstigetriturated with a small amount of CH2Cl2
5. 5
   SonstigeThe combined solids were dried

Vorschrift

To a solution of N-methoxy-N-methyl-1H-indazole-3-carboxamide (12.4 g, 60.42 mmol) in CH2Cl2 (200 mL) was added bis(trifluoroacetoxy)iodobenzene (28.78 g, 66.74 mmol), followed by dropwise addition of iodine (9.22 g, 36.33 mmol) in CH2Cl2 at rt. The reaction was stirred overnight, after which 300 mL saturated NaHSO3 was added and a solid began to precipitate, which was then filtered. The filtrate was concentrated and triturated with a small amount of CH2Cl2. The combined solids were dried to give 5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide (14.4 g, 72%) as a yellow solid.

Quelle