Monoperoxyphthalic Acid Magnesium Salt → 4-{2-[3,4-Bis(difluoromethoxy)phenyl]-2-{6-[4-(trifluoromethoxy)phenoxy]-3-pyridyl}ethyl}pyridine-N-oxide

HRID 567948Notes

Reaction equation

HRID 567948 reaction equation
[F:1][CH:2]([F:40])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:22]2[CH:23]=[N:24][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=3)=[CH:26][CH:27]=2)[CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[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:48])C(C(O[O-])=O)=CC=1.[Mg+2]>C(Cl)Cl.CO>[F:40][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:22]2[CH:23]=[N:24][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=3)=[CH:26][CH:27]=2)[CH2:15][C:16]2[CH:21]=[CH:20][N+:19]([O-:48])=[CH:18][CH:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12]

Participants

5

Reactant 2

HCID 10130449Monoperoxyphthalic Acid Magnesium Salt2×HCID 212627884-{2-[3,4-Bis(difluoromethoxy)phenyl]-2-{6-[4-(trifluoromethoxy)phenoxy]-3-pyridyl}ethyl}pyridine

Product 1

HCID 212628044-{2-[3,4-Bis(difluoromethoxy)phenyl]-2-{6-[4-(trifluoromethoxy)phenoxy]-3-pyridyl}ethyl}pyridine-N-oxideYield 162%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{2-[3,4-bis(difluoromethoxy)phenyl]-2-{6-[4-(trifluoromethoxy)phenoxy]-3-pyridyl}ethyl}pyridine (340 mg, 0.598 mmol) from Step 5 above in a mixture of 6 mL of CH2Cl2 and 0.6 mL of MeOH, was added MMPP (222 mg, 0.359 mmol) in one portion. The mixture was stirred 24 h at room temperature and the reaction was completed with an other 50 mg of MMPP. The reaction was 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 (5% MeOH/CH2Cl2) to afford the title compound as an amorphous solid (340 mg, 97%).

Workup

  1. customThe reaction was quenched 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 (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ebb6f3d8ed0940de80ad1768c155f568
Source dataset
uspto-grants-2001_01
Patent number
US06180650B2

Reaction notes

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