Adding a certain compound to certain chemical reactions, such as: 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 17564-64-6, COA of Formula: C9H6ClNO2
A solution of benzyl (2S,5S)-2,5-dimethyl-4-oxo-piperidine-1-carboxylate (46.3 g, 177.2 mmol) in THF (280 mL) was cooled to -78 C before LiHMDS (1 M in THF) (212 mL of 1 M, 212 mmol) was added at such a rate as to keep the temperature below -65 C. On complete addition, the mixture was stirred at -78 C for a further 10 minutes before a solution of 2- (chloromethyl)isoindoline-1,3-dione (41.6 g, 213 mmol) in THF (230 mL) was added at such a rate as to keep the temperature below -65 C. On complete addition, the dry ice/acetone cooling bath was removed and the reaction flask was placed in an ice/water bath. The reaction mixture was allowed to warm to 0 C over 30 minutes. The mixture was re-cooled to -78 C before being quenched carefully with saturated aqueous NH4Cl solution (93 mL) at such a rate as to keep the internal temp below -65 C. On complete addition the cooling bath was removed and the mixture allowed to warm to ambient temperature. EtOAc (500 mL) was added and the organic phase separated. The organic phase was washed with water (x 2), brine, dried (MgSO4), filtered and concentrated in vacuo. IPA (500 mL) was added to the residue and the resulting solution left to stand over the weekend. The resulting crystallised solid was collected by filtration, washed with minimal IPA and dried under vacuum to give benzyl (2S,3S,5S)-3-[(1,3-dioxoisoindolin-2- yl)methyl]-2,5-dimethyl-4-oxo-piperidine-1-carboxylate (31 g, 42%) as a colourless solid; 1H NMR (400 MHz, DMSO-d6) delta 7.95 – 7.78 (m, 5H), 7.49 – 7.24 (m, 6H), 5.25 – 5.07 (m, 2H), 4.73 – 4.53 (m, 1H), 4.33 (t, 1H), 3.95 – 3.75 (m, 2H), 3.01 (s, 2H), 2.70 – 2.57 (m, 1H), 1.11 (d, 3H), 0.88 (d, 3H); MS m/z: 421 (M+H)+.
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Reference:
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BAYLY, Andrew; BLEICH, Matthew; CHARRIER, Jean-Damien; DODD, James; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KELLY, Shazia; KNEGTEL, Ronald; MOCHALKIN, Igor; MORTIMORE, Michael; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; RUTHERFORD, Alistair; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (1159 pag.)WO2019/148132; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem