Dichloromethane → 4-{2-[3,4-Bis(difluoromethoxy)phenyl]-2-{6-[4-(methoxycarbonyl)phenoxy]-3-pyridyl}ethyl}pyridine-N-oxide

HRID 567950Notes

Reaction equation

HRID 567950 reaction equation
[F:1][CH:2]([F:41])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:23]2[CH:24]=[N:25][C:26]([O:29][C:30]3[CH:35]=[CH:34][C:33](OC(F)(F)F)=[CH:32][CH:31]=3)=[CH:27][CH:28]=2)[CH2:15][C:16]2[CH:21]=[CH:20][N+:19]([O-:22])=[CH:18][CH:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12].C1C=C(C([O-])=O)C([C:51]([O:53][O-])=[O:52])=CC=1.[Mg+2].[CH2:56](Cl)Cl>CO>[F:41][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:23]2[CH:24]=[N:25][C:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([C:51]([O:53][CH3:56])=[O:52])=[CH:34][CH:35]=3)=[CH:27][CH:28]=2)[CH2:15][C:16]2[CH:17]=[CH:18][N+:19]([O-:22])=[CH:20][CH:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:12])[F:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 212628044-{2-[3,4-Bis(difluoromethoxy)phenyl]-2-{6-[4-(trifluoromethoxy)phenoxy]-3-pyridyl}ethyl}pyridine-N-oxide

Product 1

HCID 212627854-{2-[3,4-Bis(difluoromethoxy)phenyl]-2-{6-[4-(methoxycarbonyl)phenoxy]-3-pyridyl}ethyl}pyridine-N-oxideYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-{2-[3,4-bis(difluoromethoxy)phenyl]-2-{6-[4-(methoxycarbonyl)phenoxy]-3-pyridyl}ethyl}pyridine from Example 1 (249 mg, 0.46 mmol) in a mixture of 5 mL of CH2Cl2 and 0.5 mL of MeOH, was added MMPP (171 mg, 0.28 mmol) in one portion. The mixture was stirred 24 h at room temperature, quenched with a saturated aqueous NaHCO3 solution and diluted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (Gradient 20% to 40% EtOHiethyl acetate) to afford the title compound as a viscous oil (260 mg, 71%).

Workup

  1. customquenched with a saturated aqueous NaHCO3 solution
  2. additiondiluted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (Gradient 20% to 40% EtOHiethyl acetate)

Sources & evidence

ORD record
ord-eef872a62d914e769efffb63e50fd436
Source dataset
uspto-grants-2001_01
Patent number
US06180650B2

Reaction notes

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