Pyrrolidine → Z-6-Chloro-3-[5-chloro-2-(3-methyl-oxetan-3-ylmethoxy)-benzylidene]-1,3-dihydro-indol-2-one

HRID 504490Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To the mixture of 5-chloro-2-(3-methyl-oxetan-3-ylmethoxy)-benzaldehyde (2 g, 8.3 mmol) and 6-Chloro-1,3-dihydro-indol-2-one (1.27 g, 7.6 mmol) in methanol (20 mL) was added pyrrolidine (0.6 g, 9.1 mmol) dropwise. The mixture was then heated at 70° C. for 2 h. After cooled to room temperature, the mixture was filtered and resulting precipitate was collected, dried to give title compound as a yellow solid (2.3 g).

Workup

temperatureAfter cooled to room temperature
filtrationthe mixture was filtered
customresulting precipitate
customwas collected
customdried

Sources & evidence

ORD record: ord-f06c8a05869d405c823e2fcc071c8362
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776875B2

Reaction notes

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