Reacción #1274513

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

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto precipitate which
2. 2
   Filtraciónwas filtered
3. 3
   Lavadorinsed with excess DCM
4. 4
   LavadoThe filtrate was washed with brine
5. 5
   Secadodried over MgSO4
6. 6
   Concentraciónconcentrated
7. 7
   Otrothe remaining solid was triturated with a minimal amount of DCM
8. 8
   SecadoThe combined solids were dried under vacuum over KOH

Procedimiento

To the N-methoxy-N-methyl-1H-indazole-3-carboxamide (XVI) (20 g, 97.4 mmol) in DCM (1 L) was added bis(trifluoroacetoxy)iodobenzene (46 g, 107 mmol) followed by portionwise addition of iodine (14.84 g, 58.5 mmol) at room temperature. After 1 hour, 600 mL of saturated NaHSO3 was added and a solid began to precipitate which was filtered and rinsed with excess DCM. The filtrate was washed with brine, dried over MgSO4, concentrated and the remaining solid was triturated with a minimal amount of DCM. The combined solids were dried under vacuum over KOH to produce 5-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamide (XVII) as a white solid (23.2 g, 70 mmol, 72% yield). 1H NMR (DMSO-d6) δ ppm 3.45 (s, 4H), 3.77 (s, 4H), 7.45-7.54 (m, 1H), 7.66 (dd, J=8.81, 1.51 Hz, 1H), 8.40 (d, J=1.01 Hz, 1H); ESIMS found for C10H10IN3O2 m/z 331 (M+H).

Fuente