Acetonitrile → [5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amine

HRID 2080471Notes

Reaction equation

HRID 2080471 reaction equation
[C:1](#[N:3])[CH3:2].[Cl:4][C:5]1[C:6]([CH:23]([S:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])=CC(NCC2C=CC(OC)=C(OC)C=2)=N[CH:10]=1.[N+:42]([O-])([O-])=O.[NH4+].[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(=O)(O)[O-].[Na+]>O>[Cl:4][C:5]1[C:6]([CH:23]([S:32]([C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)(=[O:33])=[O:34])[C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])=[CH:2][C:1]([NH2:42])=[N:3][CH:10]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 231147515-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine

Product 1

HCID 23114671[5-Chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amineYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an acetonitrile (4 ml)/water (1 ml) mixed solution of the 5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine (43 mg, 0.074 mmol) obtained in Example 186 was added cerium (IV) diammonium nitrate (100 mg) under ice cooling. The resulting mixture was stirred for 1.5 hours. To the reaction mixture was added saturated sodium bicarbonate, followed by extraction with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was purified by silica gel thin-layer chromatography (hexane:ethyl acetate=3:1) to give the title compound (12 mg, 0.028 mmol, 38%) as a pale yellowish white powder.

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel thin-layer chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-2ff93e0a106c4ac5bac60f62f77092a8
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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