HCID 17980516, compound → HCID 17980557, compound

HRID 1784104Notes

Reaction equation

HRID 1784104 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[C:19](I)=[CH:18][CH:17]=[C:16]3[O:21][CH2:22][O:23][C:15]=13)=[CH:10][C:9]([O:24][CH3:25])=[C:8]([O:26][CH3:27])[CH:7]=2)#[N:2].[C:28](C1C=NC2C(C=1NC1C(I)=CC(I)=C3OCOC=13)=CC(OC)=C(OC)C=2)#[N:29]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[C-]#N.[Zn+2].[C-]#N.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].[Zn].CC(N(C)C)=O>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[C:19]([C:28]#[N:29])=[CH:18][CH:17]=[C:16]3[O:21][CH2:22][O:23][C:15]=13)=[CH:10][C:9]([O:24][CH3:25])=[C:8]([O:26][CH3:27])[CH:7]=2)#[N:2]

Participants

8

Reactant 2

HCID 17980516HCID 17980516, compoundHCID 17980541HCID 17980541, compound

Product 1

HCID 17980557HCID 17980557, compound

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 15826098Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+)CatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

Tris(dibenzylideneacetone)dipalladium (0.039 g) was added to a mixture of a 4:1 mixture (0.25 g) of 3-cyano-4-(6-iodo-2,3-methylenedioxyanilino)-6,7-dimethoxyquinoline and 3-cyano-4-(4,6-diiodo-2,3-methylenedioxyanilino)-6,7-dimethoxyquinoline (Example 10, Note [11]), zinc cyanide (0.092 g), diphenylphosphinoferrocene (0.046 g), zinc powder (0.017 g) and DMA (15 ml) and the resultant mixture was stirred and heated to 110° C. for 1 hour. The mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulphate and evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of hexane and ethyl acetate as eluent. There were thus obtained in turn:—

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customevaporated
  5. customthe residue was purified by column chromatography on silica using
  6. temperatureincreasingly polar mixtures of hexane and ethyl acetate as eluent
  7. customThere were thus obtained in turn

Sources & evidence

ORD record
ord-73684015d8eb4a0593744711924a72c2
Source dataset
uspto-grants-2009_03
Patent number
US07501516B2

Reaction notes

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