Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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. Application In Synthesis of 2-(Bromomethyl)isoindoline-1,3-dione
(S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethoxycarbonyl)-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate To a mixture of No. 5447725 (Compound G; 40 mg, 0.07 mmol), DBU (26 muL, 0.171 mmol), and dichloromethane (0.57 mL) was added 2-bromomethyl-isoindole-1,3-dione (41 mg, 0.171 mmol) commercially available from Aldrich (cat. No. 252611-5G). After the mixture was stirred at room temperature for 17 hours, further 2-bromomethyl-isoindole-1,3-dione (41 mg, 0.171 mmol) and DBU (9 muL, 0.057 mmol) were added. After further 2 hours, the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethyl) 1-butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethoxycarbonyl)-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate (51 mg, 89%; ESI (LC/MS positive mode) m/z 1018 (M+H); Rt 3.40 min.).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5332-26-3, its application will become more common.
Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; KOHCHI, Yasunori; NAKAMA, Kimitaka; KOMIYAMA, Susumu; WATANABE, Fumio; EP2886530; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem