Monoperoxyphthalic Acid Magnesium Salt → HCID 22350136, compound

HRID 896708Notes

Reaction equation

HRID 896708 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([CH:20]=[C:21]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[C:22]#[N:23])[CH:17]=[CH:18][CH:19]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2].C1C=C(C([O-])=[O:37])C(C(O[O-])=O)=CC=1.[Mg+2]>C(Cl)Cl.CO.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([CH:20]4[O:37][C:21]4([C:24]4[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=4)[C:22]#[N:23])[CH:17]=[CH:18][CH:19]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 69693749HCID 69693749, compound

Product 1

HCID 22350136HCID 22350136, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of 3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-pyridin-4-yl-acrylonitrile from Step 1 (75 mg, 0.3 mmol) in CH2Cl2/MeOH (1:1, 2 mL) was added MMPP (148 mg, 0.3 mmol). The resulting reaction mixture was stirred 18 h at 21° C., then 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 EtOH/ethyl acetate, 10:90) provided the title compounds.

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 EtOH/ethyl acetate, 10:90)

Sources & evidence

ORD record
ord-2c3fb5da5c0c442880f019938487d834
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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