Iodine → HCID 178436892, compound

HRID 340069Notes

Reaction equation

HRID 340069 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([F:11])=[CH:5][C:4]=1[C:12]1[CH:20]=[C:19]2[C:15]([CH:16]=[N:17][NH:18]2)=[CH:14][CH:13]=1)[CH3:2].[OH-].[K+].[I:23]I>CN(C=O)C.O>[CH2:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([F:11])=[CH:5][C:4]=1[C:12]1[CH:20]=[C:19]2[C:15]([C:16]([I:23])=[N:17][NH:18]2)=[CH:14][CH:13]=1)[CH3:2]

Participants

6

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 71238203HCID 71238203, compound

Product 1

HCID 178436892HCID 178436892, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-(2-ethyl-5-fluoro-4-methoxy-phenyl)-1H-indazole (Preparation 15, 1.46 g, 5.4 mmol) in DMF (20 mL) was added KOH (1.14 g, 20.3 mmol) and the mixture was stirred for 5 minutes. A solution of iodine (2.75 g, 10.8 mmol) in DMF (5 mL) was slowly added and the reaction was stirred at room temperature for 30 minutes. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL). The organic layer was washed with water (2×100 mL) and saturated sodium metabisulfite aqueous solution (100 mL), dried over MgSO4 and concentrated in vacuo to furnish the title compound (1.94 g) in a 91% yield.

Workup

  1. stirringthe reaction was stirred at room temperature for 30 minutes
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with water (2×100 mL) and saturated sodium metabisulfite aqueous solution (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc85504c53544bd98d99229e4b84d251
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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