Iodine → HCID 70983967, compound

HRID 1775571Notes

Reaction equation

HRID 1775571 reaction equation
[C:1]([NH:4][C:5]1[N:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:6]=1)(=[O:3])[CH3:2].[I:23](O)(=O)=O.II>C(O)C>[C:1]([NH:4][C:5]1[N:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=[C:7]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[C:6]=1[I:23])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 24345Iodic acidHCID 70983988HCID 70983988, compound

Product 1

HCID 70983967HCID 70983967, compoundYield 397.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-(5-acetamido-3-(4-fluorophenyl)-1H-pyrazol-1-yl)acetate (1.1 g, 3.7 mmol) in ethanol (33 mL) were added iodic acid (170 mg, 0.95 mmol) and iodine (480 mg, 1.9 mmol). The reaction was stirred for 90 min at 60° C. The reaction mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2 and washed with a 2 N Na2SO3 solution. The organic phase was dried over MgSO4, filtered and evaporated to give ethyl 2-(5-acetamido-3-(4-fluorophenyl)-4-iodo-1H-pyrazol-1-yl)acetate as a white solid (1.63 g), which was used as such in the subsequent step.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with a 2 N Na2SO3 solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3d5d10e8e09940e3af2cec73dcb4c74a
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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