Iodine → HCID 57535432, compound

HRID 1455633Notes

Reaction equation

HRID 1455633 reaction equation
N[C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[I:18]I.N([O-])=O.[Na+]>CC(O)=O.C(Cl)Cl.CCOC(C)=O.O>[I:18][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 807IodineHCID 23668193Sodium NitriteHCID 68960107HCID 68960107, compound

Product 1

HCID 57535432HCID 57535432, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21922555Acetic acid methylene chlorideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 3-amino-2-[4-(methylsulfonyl)phenyl]pyridine (1.0 eq.) in AcOH:CH2Cl2 (1:1, 0.13 M) at −20° C. was added I2 (1.5 eq), KI (1.5 eq) then NaNO2(1.5 eq). The mixture was stirred at 20° C. for 2 h then diluted with EtOAc and water. The organic extracts were washed with aqueous NaHCO3, brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 40:60) afforded the title compound as a white solid.

Workup

  1. washThe organic extracts were washed with aqueous NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-08616e09b8fc4d4ea5e35e3b6622eb09
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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