Iodine → 5-(4-Chlorophenyl)-2-iodopyridine

HRID 1916546Notes

Reaction equation

HRID 1916546 reaction equation
C(ON=O)(C)(C)C.[I:8]I.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20](N)=[N:21][CH:22]=2)=[CH:13][CH:12]=1.C(Cl)Cl>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O.O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([I:8])=[N:21][CH:22]=2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 807Iodine2×HCID 6344DichloromethaneHCID 10906Tert-Butyl nitrite2×HCID 132426445-(4-Chlorophenyl)pyridin-2-amine

Product 1

HCID 859698495-(4-Chlorophenyl)-2-iodopyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

40.5 mL (33 mmol) tert-butylnitrite and 54 g (210 mmol) iodine are added to a solution of 38 g (190 mmol) 5-(4-chloro-phenyl)-pyridin-2-ylamine in 400 mL carbon tetrachloride in a flask protected from light and the mixture is stirred for 72 h at RT. A further 40.5 mL (33 mmol) tert-butylnitrite, 54 g (210 mmol) iodine and 100 mL DCM are added. The reaction solution is stirred for a further 24 h at RT. The solvent is eliminated i.vac. and the residue taken up in 125 mL EtOAc and 50 mL water. The aqueous phase is extracted once with EtOAc. The organic phase is dried over Na2SO4 and stirred for one night over activated charcoal. After filtration the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (PE/EtOAc 9:1).

Workup

  1. stirringThe reaction solution is stirred for a further 24 h at RT
  2. extractionThe aqueous phase is extracted once with EtOAc
  3. dry with materialThe organic phase is dried over Na2SO4
  4. stirringstirred for one night over activated charcoal
  5. filtrationAfter filtration the solvent
  6. customFurther purification

Sources & evidence

ORD record
ord-03efe609d86249bcad7106ace66a37b6
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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