Iodine → Methyl 5-iodo-1H-indazole-3-carboxylate

HRID 2307814Notes

Reaction equation

HRID 2307814 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][N:6]=1)=[O:4].FC(F)(F)C(OC1C(OC(=O)C(F)(F)F)=C([I:25])C=CC=1)=O.II.S(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([I:25])[CH:12]=2)[NH:7][N:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 807IodineHCID 657476methyl 1H-indazole-3-carboxylateHCID 12041285BistrifluoroacetoxyiodobenzeneHCID 23665763Sodium Bisulfite

Product 1

HCID 12689370Methyl 5-iodo-1H-indazole-3-carboxylateYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 271A (300 mg; 1.7 mmol), bis(trifluoroacetoxy)iodobenzene (800 mg; 1.9 mmol), and iodine (253 mg; 1.0 mmol) in CH2Cl2 (10 mL) was stirred overnight at r.t., and treated with sodium bisulfite (aq). The precipitate was collected, rinsed with water and hexane, and dried under vacuum to provide the desired product (180 mg; 36%).

Workup

  1. customThe precipitate was collected
  2. washrinsed with water and hexane
  3. customdried under vacuum

Sources & evidence

ORD record
ord-6a826437bbbf4e1a8ae6e74207f3e971
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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