Piperidine → 1-(5-Bromo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one

HRID 991843Notes

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.[O:12]=[C:13]1[C:18]2=[CH:19][NH:20][C:21]([CH:22]=O)=[C:17]2[CH2:16][CH2:15][NH:14]1.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:22][C:21]1[NH:20][CH:19]=[C:18]2[C:17]=1[CH2:16][CH2:15][NH:14][C:13]2=[O:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-bromo-1,3-dihydro-indol-2-one (23 mg, 0.11 mmol), 4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridin-1-carbaldehyde (29.7 mg, 0.18 mmol) and 0.1 mL of piperidine in ethanol (1 mL) was heated in a sealed tube at 80° C. for 4 hours. The precipitate was collected by vacuum filtration, washed with cold ethanol and dried to give 26 mg (67%) of the title compound.

Workup

filtrationThe precipitate was collected by vacuum filtration
washwashed with cold ethanol
customdried

Sources & evidence

ORD record: ord-ac736cd5d77d46088824048c8049634d
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465507B2

Reaction notes

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