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

HRID 218459

Reaction equation

HRID 218459 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bf0c526919e04f2bb8dbe14fc2f2e7db
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Linked notes

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