Реакция #964295

Уравнение реакции

NaHSO3

iodine

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

bis(trifluoroacetoxy)iodobenzene

→

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

Выход 72.0%

Растворители

DCM

Условия реакции

Обработка

1. 1
   Другоеto precipitate which
2. 2
   Фильтрацияwas filtered
3. 3
   Промывкаrinsed with excess DCM
4. 4
   ПромывкаThe filtrate was washed with brine
5. 5
   Сушкаdried over MgSO4
6. 6
   Концентрированиеconcentrated
7. 7
   Другоеthe remaining solid was triturated with a minimal amount of DCM
8. 8
   СушкаThe combined solids were dried under vacuum over KOH

Методика

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).

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