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

HRID 504605

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

Participants

Conditions

Temperature: 70 °C

Procedure

To the mixture of 6-chloro-5-fluoro-1,3-dihydro-indol-2-one (500 mg, 2.7 mmol) and 2-(4-chloro-2-formyl-phenoxy)-2-ethyl-butyric acid methyl ester (844 mg, 2.97 mmol) in methanol (5 mL) was added pyrrolidine (95 mg, 1.35 mmol) dropwise. The mixture was then heated at 70° C. for 1 h. After cooled to room temperature, the mixture was partitioned between EtOAc and diluted HCl solution. The organic phase was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the crude product as a red-yellow solid, which was used for the next step reaction without further purification.

Workup

temperatureAfter cooled to room temperature
customthe mixture was partitioned between EtOAc and diluted HCl solution
washThe organic phase was washed with water, brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-127f6985906649c7a89aa6fa24ed79e0
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776875B2

Linked notes

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