Toluene → HCID 18518640, compound

HRID 1369102Notes

Reaction equation

HRID 1369102 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][N:21](C=O)C.[CH2:25]([N:27]([CH2:50][CH3:51])[CH2:28][CH2:29][N:30]1[C:38]2[C:33](=[C:34]([Cl:40])[CH:35]=[C:36](I)[CH:37]=2)[C:32]([OH:48])([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[Cl:47])[C:31]1=[O:49])[CH3:26].C1(C)C=CC=CC=1>CCOC(C)=O.[C-]#N.[C-]#N.[Zn+2]>[CH2:25]([N:27]([CH2:50][CH3:51])[CH2:28][CH2:29][N:30]1[C:38]2[C:33](=[C:34]([Cl:40])[CH:35]=[C:36]([C:20]#[N:21])[CH:37]=2)[C:32]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[Cl:47])([OH:48])[C:31]1=[O:49])[CH3:26]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 18518682HCID 18518682, compound

Product 1

HCID 18518640HCID 18518640, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To Pd2(dba)3CHCl3 (5.69 mg, 5 mol %) and triphenyIphosphine (5.76 mg, 20 mol %) under a nitrogen atmosphere was added anhydrous DMF (0.5 mL). The mixture was stirred at room temperature for 30 minutes to give orange/yellow mixture. To this was then added 1-(2-diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-chloro-6-iodooxindole (57.0 mg, 1.1×10−4 mol) followed by Zn(CN)2 (17.2 mg, 0.8 eq., 60%). The resulting suspension was heated to 60° C. (bath temperature) and stirred at that temperature for 3 hours. The mixture was allowed to cool and diluted with EtOAc:toluene (10 mL, 1:1). The mixture was washed with H2O (2×10 mL) and dried (anhydrous MgSO4). After filtration the solvent was removed in vacuo to give the crude title compound.

Workup

  1. customto give orange/yellow mixture
  2. temperatureThe resulting suspension was heated to 60° C. (bath temperature)
  3. stirringstirred at that temperature for 3 hours
  4. temperatureto cool
  5. washThe mixture was washed with H2O (2×10 mL)
  6. dry with materialdried (anhydrous MgSO4)
  7. filtrationAfter filtration the solvent
  8. customwas removed in vacuo

Sources & evidence

ORD record
ord-e3cd1080324e4867aab17dfecf40fbe9
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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