Pyrrolidine → Z-1-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxymethyl]-cyclopentanecarbonitrile

HRID 504532Notes

Reaction equation

HRID 504532 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:4]([CH:17]=O)[CH:3]=1.[Cl:19][C:20]1[CH:28]=[C:27]2[C:23]([CH2:24][C:25](=[O:29])[NH:26]2)=[CH:22][CH:21]=1.N1CCCC1>CO>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]2([C:13]#[N:14])[CH2:9][CH2:10][CH2:11][CH2:12]2)=[C:4](/[CH:17]=[C:24]2\[C:25](=[O:29])[NH:26][C:27]3[C:23]\2=[CH:22][CH:21]=[C:20]([Cl:19])[CH:28]=3)[CH:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 577501211-(4-Chloro-2-formyl-phenoxymethyl)-cyclopentanecarbonitrile

Product 1

HCID 86632073Z-1-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxymethyl]-cyclopentanecarbonitrileYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 1b, 1-(4-chloro-2-formyl-phenoxymethyl)-cyclopentanecarbonitrile (17.4 g, 66 mmol) was reacted with 6-chlorooxindole (8.5 g, 51 mmol) and pyrrolidine (4.69 g, 66 mmol) in methanol to give the title compound as a yellow solid (19 g).

Sources & evidence

ORD record
ord-632dd160dac14bf9a36a4fac3ec89bef
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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