Reference of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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.
Intermediate 60 : 2-(3-(3-Oxopiperazin-l-yl)propyl)isoindoline-l,3-dione (0587) A mixture of 3-(l,3-dioxoisoindolin-2-yl)propanal (499.4 mg, 2.458 mmol, commercially available from Fluorochem), piperazin-2-one (376.1 mg, 3.76 mmol, commercially available from Sigma Aldrich) and Na(0Ac)3BH (779.9 mg, 3.68 mmol) in 2-MeTHF (20 mL) was stirred at rt for 21 h 40 min. Further Na(OAc)3BH (516.6 mg, 2.437 mmol) was added after 3 h. AcOH (0.014 mL, 0.246 mmol) was added after 4 h 45 min. After 20 h 40 min further 2-MeTHF (5 mL) was added and the reaction mixture was heated to 60 C. Further Na(OAc)3BH (279.9 mg, 1.321 mmol) was added after 3 h 20 min at 60 C. Further Na(OAc)3BH (496.8 mg, 2.344 mmol) was added after 25 h 45 min at 60 C. The mixture was removed from heating and stirring after a total of 31 h at 60 C and cooled to rt. To this mixture was added sat. NaHCCte (2 mL) and water (8 mL). The mixture was stirred at rt for 20 min and extracted with EtOAc (3 x 10 mL). The organic layer was filtered through a cartridge fitted with a hydrophobic frit and the volatiles evaporated in vacuoto give an oil which was redissolved in MeOH (approx. 5 mL) and applied to the top of a 20 g Isolute aminopropyl ion exchange column. The column was eluted with 4 column volumes of MeOH and 4 column volumes of aqueous 2M HCI. The second MeOH fraction was evaporated in vacuoto give a pale yellow solid; 2-(3-(3-oxopiperazin- l-yl)propyl)isoindoline-l,3-dione (595.1 mg, 2.071 mmol, 84 % yield). (0588) LCMS (2 min high pH); Rt = 0.71 min, m/z = 288 for [MH]+
The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem