A common heterocyclic compound, the tetrahydroisoquinoline compound, name is 5-Bromo-1,2,3,4-tetrahydroisoquinoline,cas is 81237-69-6, mainly used in chemical industry, its synthesis route is as follows.
81237-69-6, A 20 mL vial was charged with 2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-151-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (0.1 g,0.332 mmol), 5-bromo-1,2,3,4-tetrahydroisoquinoline (0.083 g, 0.332 mmol), o-benzotriazol-1-yl-N,N,N’,N’-tetramethyluroniumtetrafluoroborate (0.133 g, 0.415 mmol), Hunig’s base (0.580 mL,3.32 mmol), and DMF (3 mL). The vial was sealed and stirred at room temperature. After stirring the mixture for 70.5 h, the reaction mixture was quenched withwater. The solids that formed were collected by filtration. The mother liquorwas concentrated under reduced pressure, and a second batch of solids was collected by recrystallizing from MeOH and water. 1-(5-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione (0.145 g, 0.293 mmol, 88 % yield),was isolated as an off-white solid. LC/MS: m/z 495 (M+H)+, 497.02 (M+3H)+1.935 min (method 1). 1H NMR (500 MHz, DMSO-D6) delta ppm 12.42 (s, 1H),9.22-9.27 (m, 1H), 8.18-8.31 (m, 1H), 7.84 (s, 1H), 7.09-7.59 (m, 3H),4.59-4.87 (m, 2H), 3.67-3.95 (m, 5H), 2.73-2.96 (m, 2H), 2.47-2.52 (m, 3H).
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Reference£º
Article; Swidorski, Jacob J.; Liu, Zheng; Yin, Zhiwei; Wang, Tao; Carini, David J.; Rahematpura, Sandhya; Zheng, Ming; Johnson, Kim; Zhang, Sharon; Lin, Pin-Fang; Parker, Dawn D.; Li, Wenying; Meanwell, Nicholas A.; Hamann, Lawrence G.; Regueiro-Ren, Alicia; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 160 – 167;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem