Pyrrolidine → HCID 68956475, compound

HRID 1728231Notes

Reaction equation

HRID 1728231 reaction equation
ClC1C=C2C(CC(=O)N2)=CC=1.COC(C1(OC2C=CC(Cl)=CC=2C=O)CCC1)=O.N1CCCC1.[CH3:35][O:36][C:37]([C:39]1([O:43][C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:45]=2[CH:51]=[C:52]2[C:60]3[C:55](=[CH:56][C:57]([Cl:61])=[CH:58][CH:59]=3)[NH:54][C:53]2=[O:62])[CH2:42][CH2:41][CH2:40]1)=[O:38]>CO>[CH3:35][O:36][C:37]([C:39]1([O:43][C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:45]=2/[CH:51]=[C:52]2\[C:53](=[O:62])[NH:54][C:55]3[C:60]\2=[CH:59][CH:58]=[C:57]([Cl:61])[CH:56]=3)[CH2:42][CH2:41][CH2:40]1)=[O:38]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 57565924HCID 57565924, compoundHCID 57566238HCID 57566238, compound

Product 1

HCID 68956475HCID 68956475, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To the mixture of 6-chlorooxindole (10 g, 60 mmol) and 1-(4-chloro-2-formyl-phenoxy)-cyclobutanecarboxylic acid methyl ester (18 g, 64 mmol) in methanol (100 mL) was added pyrrolidine (4.5 g, 63 mmol) dropwise. The mixture was then heated at 70° C. for 1 h. After cooled to room temperature, the mixture was filtered and the precipitate was collected, dried to give a mixture of E/Z 1-[4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-cyclobutanecarboxylic acid methyl ester (6 g, 24%).

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationthe mixture was filtered
  3. customthe precipitate was collected
  4. customdried
  5. customto give

Sources & evidence

ORD record
ord-2f1f62081ac3492384d3f3c0cc6663aa
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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