N-Iodosuccinimide → 2-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-4-iodo-1-methyl-1H-pyrazol-3-yl)oxy}ethyl acetate

HRID 1062781Notes

Reaction equation

HRID 1062781 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:12]=[C:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[N:10]([CH3:27])[N:9]=1)(=[O:3])[CH3:2].[I:28]N1C(=O)CCC1=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C.O.[Cl-].[Na+].O>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([I:28])=[C:11]([NH:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:21][CH:22]=2)(=[O:15])=[O:16])[N:10]([CH3:27])[N:9]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 3

HCID 120273N-IodosuccinimideHCID 656671Sodium PyrosulfiteHCID 222819172-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazol-3-yl)oxy}ethyl acetate

Product 1

HCID 222820342-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-4-iodo-1-methyl-1H-pyrazol-3-yl)oxy}ethyl acetate

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 2-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazol-3-yl]oxy}ethyl acetate (Preparation 8) (1.15 g) in solution in tetrahydrofuran (200 ml) was added portionwise N-iodosuccinimide (18 g), at room temperature. The reaction mixture was stirred at room temperature for 2 hours. The reaction was then diluted with ethyl acetate (150 ml), water (50 ml) and brine (50 ml). A 1M solution of sodium metabisulphite (100 ml) was added and the organic layer separated. The organics were washed successively with a diluted solution of sodium metabisulphite (100 ml) and then brine (50 ml). The solution was dried on magnesium sulfate, filtered and concentrated under reduced pressure to yield the desired product as an off pink solid (33.6 g)

Workup

  1. customat room temperature
  2. customthe organic layer separated
  3. washThe organics were washed successively with a diluted solution of sodium metabisulphite (100 ml)
  4. customThe solution was dried on magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74ec89629fd545279b8ad429aa78ed1f
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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