Pyrrolidine → Z-2-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-fluoro-phenoxy]-2-methyl-propionic acid methyl ester

HRID 658945Notes

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.[CH3:12][O:13][C:14](=[O:29])[C:15]([O:18][C:19]1[CH:24]=[C:23]([F:25])[C:22]([Cl:26])=[CH:21][C:20]=1[CH:27]=O)([CH3:17])[CH3:16].N1CCCC1>CO>[CH3:12][O:13][C:14](=[O:29])[C:15]([O:18][C:19]1[CH:24]=[C:23]([F:25])[C:22]([Cl:26])=[CH:21][C:20]=1/[CH:27]=[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)([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 70 °C

Procedure

To the mixture of 6-chloro-1,3-dihydro-indol-2-one (0.73 g, 4.4 mmol) and 2-(4-Chloro-5-fluoro-2-formyl-phenoxy)-2-methyl-propionic acid methyl ester (1 g, 3.65 mmol) in methanol (15 mL) was added pyrrolidine (0.26 g, 4.4 mmol) dropwise. Then the mixture was heated at 70° C. for 1 h. After cooled to room temperature, the mixture was concentrated to give the crude product which was used for the next step reaction without further purification.

Workup

temperatureAfter cooled to room temperature
concentrationthe mixture was concentrated

Sources & evidence

ORD record: ord-1dd102f05ed84af0826a15e1221c225d
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076482B2

Reaction notes

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