Analyzing the synthesis route of 215798-19-9

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,belong tetrahydroisoquinoline compound

As a common heterocyclic compound, it belong tetrahydroisoquinoline compound,6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,215798-19-9,Molecular formula: C9H11BrClN,mainly used in chemical industry, its synthesis route is as follows.,215798-19-9

Step C: Preparation of Intermediate (R)-6-(4-(2-(2-Methylpyrrolidin-1- yl)ethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline. To a round-bottom flask was added 6-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.00 g, 8.05 mmol), (R)-4-(2-(2-methylpyrrolidin- 1 -yl)ethyl)phenylboronic acid (2.063 g, 8.85 mmol), tetrakis(triphenylphosphine)palladium (0) (0.279 g, 0.24 1 mmol), benzene (30.00 mL), ethanol (10.00 mL), and 2.0 M aqueous solution of sodium bicarbonate(8.05 mL, 16.09 mmol). The reaction mixture was refluxed for 6 h. Upon completion, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated. The residue was taken up in 1 M HC1 solution and washed with ethyl acetate. The aqueous layer was basified with 10% aqueous NaOH to pH-4 1, extracted with ethyl acetate, and concentrated. The residue was purified by silica gel column,eluting with 5-10% 2.0 M ammonia in methanol/DCM to give a yellow solid (1.20 g). LCMSm/z = 321.4 [M+H] ?H NMR (400 MHz, DMSO-d6) oe ppm 0.99-1.04 (m, 3H), 1.22-1.33 (m,1H), 1.59-1.69 (m, 2H), 1.81-1.92 (m, 1H), 2.13 (q, J= 8.67 Hz, 1H), 2.20-2.34 (m, 2H), 2.65-2.83 (m, 5H), 2.94-3.04 (m, 3H), 3.10-3.18 (m, 1H), 3.91 (s, 2H), 7.09 (d, J= 8.08 Hz, 1H),7.29 (d, J = 8.08 Hz, 2H), 7.33-7.40 (m, 2H), 7.53 (d, J = 8.08 Hz, 2H).

With the synthetic route has been constantly updated, we look forward to future research findings about 6-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride,belong tetrahydroisoquinoline compound

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; REN, Albert; SEMPLE, Graeme; TRAN, Thuy-Anh; WEI, Zheng; GROTTICK, Andrew J.; MILLS, David M.; SMITH, Brian M.; WO2014/28322; (2014); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem