Monoperoxyphthalic Acid Magnesium Salt → 8-{3-[1-(4-Chloro-phenyl)-2-(1-oxy-pyridin-4-yl)-ethyl]-phenyl}-6-isopropyl-quinoline

HRID 896685Notes

Reaction equation

HRID 896685 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:17]=[C:18]([C:22]3[CH:23]=[C:24]([CH:32]([CH3:34])[CH3:33])[CH:25]=[C:26]4[C:31]=3[N:30]=[CH:29][CH:28]=[CH:27]4)[CH:19]=[CH:20][CH:21]=2)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C1C=C(C([O-])=[O:42])C(C(O[O-])=O)=CC=1.[Mg+2]>C(Cl)Cl.CO.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[CH3:33][CH:32]([C:24]1[CH:25]=[C:26]2[CH:27]=[CH:28][CH:29]=[N:30][C:31]2=[C:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:9][C:10]3[CH:11]=[CH:12][N+:13]([O-:42])=[CH:14][CH:15]=3)[CH:17]=2)[CH:23]=1)[CH3:34]

Participants

6

Reactant 2

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 101831968-(3-(1-(4-Chlorophenyl)-2-(pyridin-4-yl)ethyl)phenyl)-6-isopropylquinoline

Product 1

HCID 102059788-{3-[1-(4-Chloro-phenyl)-2-(1-oxy-pyridin-4-yl)-ethyl]-phenyl}-6-isopropyl-quinoline

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of Example 60 (100 mg, 0.22 mmol) in CH2Cl2/MeOH (1:1, 6 mL) was added MMPP (320 mg, 0.65 mmol). After 18 h, the resulting reaction mixture was diluted with a sodium bicarbonate solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with ethanol/ethyl acetate, 10:90 to 25:75) provided the title compound.

Workup

  1. customthe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with ethanol/ethyl acetate, 10:90 to 25:75)

Sources & evidence

ORD record
ord-c0af372188c1414f9ec337d53316ca98
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

Loading…