Iodine → HCID 178438826, compound

HRID 246766Notes

Reaction equation

HRID 246766 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([CH3:3])[CH3:2].[OH-].[K+].[I:15]I.[O-]S([O-])=O.[Na+].[Na+]>CS(C)=O>[I:15][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)[NH:9][N:8]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24437Sodium SulfiteHCID 213385035-isopropyl-1H-indazole

Product 1

HCID 178438826HCID 178438826, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution containing mainly 5-isopropyl-1H-indazole (0.85 g, crude) in 70 mL of DMSO was added KOH (0.52 g, 8 mmol) at room temperature. Then I2 (1.35 g, 5.3 mmol) was added slowly, after the addition, the mixture was stirred at room temperature for 2 hours. The mixture was poured into 200 mL of saturated Na2SO3 solution, then extracted with ethyl acetate (2×100 mL). The combined organic layers was washed with water (100 mL) and brine (100 mL) dried over Na2SO4 and concentrated under reduced pressure to give crude 3-iodo-5-isopropyl-1H-indazole (0.78 g). LCMS: (M+H)+=287.

Workup

  1. additionafter the addition
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layers was washed with water (100 mL) and brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4916e2c52984335a49b1ada62cea187
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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