Pyrrolidine → Z-3-[4-Bromo-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2,2-dimethyl-propionic acid methyl ester

HRID 1728179Notes

Reaction equation

HRID 1728179 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]([CH3:17])([CH3:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[CH:14]=O.[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>[CH3:1][O:2][C:3](=[O:18])[C:4]([CH3:17])([CH3:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1/[CH:14]=[C:24]1\[C:25](=[O:29])[NH:26][C:27]2[C:23]\1=[CH:22][CH:21]=[C:20]([Cl:19])[CH:28]=2

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 575659193-(4-Bromo-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl ester

Product 1

HCID 86617597Z-3-[4-Bromo-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2,2-dimethyl-propionic acid methyl esterYield 53.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in Example 227b, 3-(4-bromo-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl ester (3.4 g, 10.8 mmol) was reacted with 6-chlorooxindole (1.8 g, 10.8 mmol) and pyrrolidine (0.84 g, 11.8 mmol) in methanol to give E/Z-3-[4-Bromo-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2,2-dimethyl-propionic acid methyl ester as a yellow solid (2.7 g).

Sources & evidence

ORD record
ord-df93e7a109e243b0a8765fabc23fc551
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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