18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 4,7-Dichloroindoline-2,3-dione
4,7-Dichloro-3-hydroxy-3-(2-oxo-2-(4-(pyrrolidin-l-yl)phenyl)ethyl)indolin-2-one (EXAMPLE 10): To 4,7-dichloroindoline-2,3-dione (A) (12.5 g, 0.06 mol) in 800 mL of methanol were added l-(4-(pyrrolidin-l-yl)phenyl)ethanone (B) (45 g, 0.24 mol) and 0.5 mL of diethylamine (2). The reaction was stirred at rt for 24 hours. The solvent was removed and the residue was purified with flash chromatography (0-5% Methanol/CLLCn) to get 13.5 g of brown solid. It was purified again with flash chromatography using ethyl acetate/hexane to give 11.5 g of an off white solid. Repeating the reaction at the same scale to give another 11.5 g of product. Two batches of product were combined and recrystallized from methanol to get 20.5 g as an off white solid. 4,7-Dichloro-3-hydroxy-3-(2-oxo-2-(4-(pyrrolidin-l- yl)phenyl)ethyl)indolin-2-one (EXAMPLE 10): off-white solid; 1H NMR (DMSO-d6, 400 MHz) delta 1.96 (m, 4H), 3.30 (m, 4H), 3.65 (d, 1H, J=16 Hz), 4.29(d, 1H, J=16Hz), 6.34 (s, 1H), 6.53(d, 2H, J=8Hz), 6.88(d, 1H, J=8Hz), 7.28 (d, 1H, J=8Hz), 7.72 (d, 2H, J=8Hz), 10.97(s, 1H). Chiral separation was performed on under the following conditions. Preparatory method utilized the following:a RegisCell column L: 250 mm, IS: 50 mm, particle size: 5 mum; mobile phase: methanol/CO2, ratio: 35/65, detection wavelength: 254 nm, flow rate: 325 g/min, co-solvent flow rate 113.75 ml/min. Dissolved 19.72 g in 1000 ml of methanol, for a concentration of 0.020 g/ml. The injection volume was 25.00 ml for a total amount 0.500 g/injection. Yield was (+): 9.73 g, with optical rotation +247 at 20 C and (-): 9.26 g.
The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TOKALAS, INC.; VERNIER, Jean-michael; (82 pag.)WO2016/57698; (2016); A1;,
Indoline – Wikipedia,
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