Iodine → HCID 178455023, compound

HRID 246718

Reaction equation

HRID 246718 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[K+].[I:20]I>CS(C)=O>[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[I:20])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

Product 1

HCID 178455023HCID 178455023, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 5-(tert-butyldimethylsilyloxy)-1H-indazole (5.3 g, 0.02 mol) in DMSO (50 mL) at 0° C., was added KOH (3.36 g, 0.06 mol) followed by iodine (10.2 g, 0.04 mol) portionwise. The mixture was stirred at room temperature for additional 10 minutes, then the reaction was quenched with 10% Na2S2O3 and diluted with water. The mixture was filtered and the filter cake was washed with water and dried to give 5-(tert-butyldimethylsilyloxy)-3-iodo-1H-indazole. The crude solid was used in the next step without purification. MS: (M+H)+=375.

Workup

  1. customthe reaction was quenched with 10% Na2S2O3
  2. additiondiluted with water
  3. filtrationThe mixture was filtered
  4. washthe filter cake was washed with water
  5. customdried

Sources & evidence

ORD record
ord-141fc4217c0e4b0dbff96dcea8947c54
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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