Reaction #1585007

Reaction equation

NaHSO3

iodine

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

bis(trifluoroacetoxy)iodobenzene

→

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

Yield 72.0%

Solvents

DCM

Conditions

Workup

1. 1
   Otherto precipitate which
2. 2
   Filtrationwas filtered
3. 3
   Washrinsed with excess DCM
4. 4
   WashThe filtrate was washed with brine
5. 5
   Dryingdried over MgSO4
6. 6
   Concentrationconcentrated
7. 7
   Otherthe remaining solid was triturated with a minimal amount of DCM
8. 8
   DryingThe combined solids were dried under vacuum over KOH

Procedure

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).

Source