Some common heterocyclic compound, 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, molecular formula is C16H20BrNO2, 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. HPLC of Formula: C16H20BrNO2
To a solution of 15 (0.4 g, 1.29 mmol) in 20 ml of dry DMF was added 0.75 g (2.31 mmol, 1.8 equiv.) of Cs2C03 and allowed to stir at room temperature for 15 minutes. Then 1.5 g (4.48 mmol, 3.5 equiv.) of bromooctyl phthalamide was added and the reaction mixture was stirred for 2 hrs at room temperature. Solvent was removed under reduced pressure and the residue purified by column chromatography (CH2Cl2:CH3OH:CH3COOH; 20: 1 :0.1) to yield 0.15 g (21 percent) of desired N-9 isomer (120c). lU NMR (500 MHz, CDC13) delta 8.18 (s, 1H), 7.71-7.75 (m, 2H), 7.60-7.64 (m, 2H), 7.21 (m, 3H), 4.13 (t, J= 7.3 Hz, 2H), 3.57 (t, J= 7.2 Hz, 2H), 1.55-1.64 (m, 4H), 1.19- 1.21 (m, 8H); 13C NMR (125 MHz, CDC13) 174.5, 167.6, 153.1, 149.9, 149.6, 144.1, 134.9, 133.0, 132.5, 131.0, 128.1, 127.9, 122.2, 48.9, 43.3, 36.9, 28.6, 27.9, 27.5, 25.7, 25.5. MS (ESI) m/z 569.22/571.13 [M+H]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17702-83-9, its application will become more common.
Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; CHIOSIS, Gabriela; YAN, Pengrong; PATEL, Pallav; PATEL, Hardik J.; TALDONE, Tony; YANG, Chenghua; SUN, Weilin; OCHIANA, Stefan; WO2015/23976; (2015); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem