Iodine → HCID 178505641, compound

HRID 1727110Notes

Reaction equation

HRID 1727110 reaction equation
[I:1]I.[OH-].[K+].[F:5][C:6]1[CH:21]=[CH:20][CH:19]=[CH:18][C:7]=1[O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[N:14][NH:15]2)=[CH:11][CH:10]=1.S(=O)(O)[O-].[Na+]>CN(C=O)C>[F:5][C:6]1[CH:21]=[CH:20][CH:19]=[CH:18][C:7]=1[O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([I:1])=[N:14][NH:15]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 575666896-(2-fluoro-phenoxy)-1H-indazole

Product 1

HCID 178505641HCID 178505641, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodine (1.53 g, 6.02 mmol) and potassium hydroxide pellets (805 mg, 14.3 mmol) were added successively into a DMF solution of 6-(2-Fluoro-phenoxy)-1H-indazole (1.35 g, 5.92 mmol) at room temperature under stirring. After 1.5 h the reaction was poured into sodium bisulfite solution and extracted into EtOAc (2×20 mL). The combined organic layers were dried over Na2SO4 filtered, concentrated and the residue was purified by flash chromatography eluting with Hex:EtOAc 9:1 to yield 1.9 g of 6-(2-fluoro-phenoxy)-3-iodo-1H-indazole: MS: 355 (M+H).

Workup

  1. extractionextracted into EtOAc (2×20 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography
  6. washeluting with Hex

Sources & evidence

ORD record
ord-5e09576259634bba9eff578beb1907a4
Source dataset
uspto-grants-2009_02
Patent number
US07495015B2

Reaction notes

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