Iodine → HCID 178504659, compound

HRID 246771Notes

Reaction equation

HRID 246771 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[CH:8]2)(=[O:4])=[O:3].[OH-].[K+].[I:16]I.O>CS(C)=O>[I:16][C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=2)[NH:10][N:9]=1

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 14797Potassium HydroxideHCID 680549865-(Methylsulfonyl)-1H-indazole

Product 1

HCID 178504659HCID 178504659, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-(methylsulfonyl)-1H-indazole (430 mg, 2.19 mmol) in DMSO (10 mL) at 0° C., were added KOH (0.4 g, 6.57 mmol) and I2 (1.2 g, 4.38 mmol) successively, then the reaction mixture was stirred at room temperature for 3 hours. Water (40 mL) was added, product extracted with EtOAc (3×30 mL), organics combined dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with petroleum ether/EtOAc=20:1) to give 3-iodo-5-(methylsulfonyl)-1H-indazole (410 mg, 59.9%) as an off-white solid. LCMS: (M+H)+=323; 1H NMR (300 MHz, DMSO): δ 7.98-7.95 (m, 4H), 3.27 (s, 3H).

Workup

  1. extractionproduct extracted with EtOAc (3×30 mL)
  2. dry with materialorganics combined dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with petroleum ether/EtOAc=20:1)

Sources & evidence

ORD record
ord-445cc500714949d99e8a06382c8b94f5
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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