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

HRID 218459

Reaktionsgleichung

Reaktionsgleichung von HRID 218459
[CH3:1][O:2][N:3]([CH3:15])[C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][N:7]=1)=[O:5].FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C([I:27])C=CC=1)=O.II.OS([O-])=O.[Na+]>C(Cl)Cl>[I:27][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:4]([N:3]([O:2][CH3:1])[CH3:15])=[O:5]

Komponenten

6

Edukt 4

HCID 807IodineHCID 12041285BistrifluoroacetoxyiodobenzeneHCID 16036867N-Methoxy-N-methyl-1H-indazole-3-carboxamideHCID 23665763Sodium Bisulfite

Produkt 1

HCID 205807385-iodo-N-methoxy-N-methyl-1H-indazole-3-carboxamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. customto precipitate
  2. filtrationwhich was then filtered
  3. concentrationThe filtrate was concentrated
  4. customtriturated with a small amount of CH2Cl2
  5. customThe combined solids were dried

Quellen und Nachweise

ORD-Eintrag
ord-bf0c526919e04f2bb8dbe14fc2f2e7db
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198456B2

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