Electric Literature of 193354-13-1,Some common heterocyclic compound, 193354-13-1, name is 5-Iodoindolin-2-one, molecular formula is C8H6INO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
3-[5-(5-Iodo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrol-3-yl]-propionic acid 3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.5 mg), 130 mg 5-iodo-2-oxindole, and 75 muL piperidine in 3 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 155 mg (71%) of the title compound as an orange solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.41 (s, br, 1H, NH-1′), 12.03 (s, br, 1H, COOH), 10.79 (s, br, 1H, NH-1), 8.12 (d, J=1.70 Hz, 1H, H-4), 7.65 (s, 1H, H-vinyl), 7.36 (dd, J=1.70, 7.93 Hz, 1H, H-6), 6.79 (d, J=7.93 Hz, 1H, H-7), 2.64 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.34 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.29 (s, 3H, CH3), 2.27 (s, 3H, CH3); MS m/z (relative intensity, %) 437 ([M+1]+, 100).
The synthetic route of 193354-13-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
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