Reacción #305641

Ecuación de reacción

NaHSO3

iodine

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

bis(trifluoroacetoxy)iodobenzene

→

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

Rendimiento 72.0%

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto precipitate
2. 2
   Filtraciónwhich was then filtered
3. 3
   ConcentraciónThe filtrate was concentrated
4. 4
   Otrotriturated with a small amount of CH2Cl2
5. 5
   OtroThe combined solids were dried

Procedimiento

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.

Fuente