Methyl Acrylate → HCID 178499873, compound

HRID 24953Notes

Reaction equation

HRID 24953 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]/[C:10](=[C:18]2\[C:19](=[O:30])[NH:20][C:21]3[C:26]\2=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)/[C:11]2[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[C:31]([O:35][CH3:36])(=[O:34])[CH:32]=[CH2:33].C(N(CC)CC)C>C(#N)C.CC(O)=O.CC(O)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]/[C:10](=[C:18]2\[C:19](=[O:30])[NH:20][C:21]3[C:26]\2=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)/[C:11]2[CH:16]=[CH:15][C:14](/[CH:33]=[CH:32]/[C:31]([O:35][CH3:36])=[O:34])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 178492234HCID 178492234, compound

Product 1

HCID 178499873HCID 178499873, compound

Reagents, catalysts & solvents 2

HCID 4144353Palladium (II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

257 mg (0.5 mmol) of (Z)-3-[1-(4-methoxyphenylamino)-1-(4-iodophenyl)-methylidene]-5-nitro-2-indolinone (Example 434), 0.06 ml (0.75 mmol) of methyl acrylate, 4.5 mg (0.02 mmol) of palladium-II-acetate and 1 ml of (7.2 mmol) of triethylamine are dissolved in 20 ml of acetonitrile under a nitrogen atmosphere. The solution is heated for 10 hours to 80° C. Then the reaction solution is filtered through Celite and the solvent is eliminated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol=20:1).

Workup

  1. temperatureThe solution is heated for 10 hours to 80° C
  2. filtrationThen the reaction solution is filtered through Celite
  3. customThe residue is chromatographed on silica gel (dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-a8310ab92a5a48f487eab88294f308ce
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

Loading…