Piperidine → 5-Bromo-3-[5-(2-dimethylamino-ethoxy)-1H-indol-2-ylmethylene]-1,3-dihydro-indol-2-one

HRID 49070Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][N:13]([CH3:28])[CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([CH:26]=O)=[CH:20]2.N1CCCCC1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:26][C:21]1[NH:22][C:23]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:16][CH2:15][CH2:14][N:13]([CH3:12])[CH3:28])=[CH:25][CH:24]=2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-bromo-2-oxindole (46 mg, 0.215 mmol), 5-(2-dimethylamino-ethoxy)-1H-indole-2-carbaldehyde (50 mg, 0.21 mmol) and piperidine (0.1 mL) in ethanol (1 mL) was heated at 100° C. for 2 hours. The precipitate was collected by vacuum filtration, washed with ethanol and dried to give 72 mg (78%) of the title compound as a red solid.

Workup

filtrationThe precipitate was collected by vacuum filtration
washwashed with ethanol
customdried

Sources & evidence

ORD record: ord-f023e8ff95fe48e3a1fe6b179c473957
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706709B2

Reaction notes

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