Piperidine → 5-Methoxy-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one

HRID 2213675Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[C:13]([C:16]1[NH:17][CH:18]=[CH:19][CH:20]=1)(=O)[CH3:14].N1CCCCC1.CCCCCC.C(OCC)(=O)C>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[C:13]([C:16]1[NH:17][CH:18]=[CH:19][CH:20]=1)[CH3:14]

Participants

Conditions

Temperature: 130 °C

Procedure

Alternatively, a mixture of 5-methoxyindolin-2-one (0.50 g, 3.1 mmol), 2-acetylpyrrole (0.28 g, 2.4 mmol) and piperidine (0.60 g, 0.6 mmol) was placed in a sealed tube and melted. The reaction vessel was sealed and the mixture was heated to 130° C. overnight. The reaction was then cooled to ambient temperature and dissolved in ethyl acetate (2 mL). Chromatography (SiO2, 15 g) using 2:1 hexane/ethyl acetate afforded 5-methoxy-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one; (0.24 g); 1H NMR (400 MHz, DMSO-d6) δ 2.78 (s, 3H), 3.82 (s, 3H), 6.38 (m, 1H), 6.70–6.80 (m, 2H), 6.98 (m, 1H), 7.16 (m, 1H), 7.30 (m, 1H), 7.68 (m, 1H) ppm.

Workup

customwas placed in a sealed tube
customThe reaction vessel was sealed
temperatureThe reaction was then cooled to ambient temperature

Sources & evidence

ORD record: ord-13d2a429d88e4c62b549a154f4f08565
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105563B2

Reaction notes

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