Pyrrolidine → Z-2-[4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-propyl-pentanoic acid ethyl ester

HRID 504585Notes

Reaction equation

HRID 504585 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15](=[O:33])[C:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[CH:31]=O)([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH3:13].N1CCCC1>CO>[CH2:12]([O:14][C:15](=[O:33])[C:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1/[CH:31]=[C:6]1\[C:7](=[O:11])[NH:8][C:9]2[C:5]\1=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH3:13]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 59428102HCID 59428102, compound

Product 1

HCID 86632098Z-2-[4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-propyl-pentanoic acid ethyl esterYield 20.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To the mixture of 6-chlorooxindole (9.3 g, 55.7 mmol) and 2-(4-chloro-2-formyl-phenoxy)-2-propyl-pentanoic acid ethyl ester (14 g, 42.9 mmol) in methanol (100 mL) was added pyrrolidine (3.3 g, 47.2 mmol) dropwise. The mixture was then heated at 80° C. for 2 h. After cooled to room temperature, the mixture was concentrated. The residue was purified by flash column to give the title compound (4.2 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe mixture was concentrated
  3. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-f817215d9c1e4c3eb3f12dab9d16abf1
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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