The tetrahydroisoquinoline compound, cas is 923591-51-9 name is 5-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride, mainly used in chemical industry, its synthesis route is as follows.
Intermediate O: 5-(2-(l-Methyl-lH-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-l,2,3,4- tetrahydroisoquinoline A vial was charged with 5-bromo-l,2,3,4-tetrahydroisoquinoline hydrochloride (ASW Medchem, Brunswick, NJ, 400.42 mg, 1.367 mmol), (2-(l- methyl-lH-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)boronic acid (Intermediate B, 443 mg, 1.640 mmol), potassium phosphate (1 160 mg, 5.47 mmol), and Pd(AmPhos)2Ci2 (Sigma- Aldrich, St. Louis, MO, 48.4 mg, 0.068 mmol). The vial was flushed with Ar (g), then dioxane (2928 mu) and water (976 mu) were added in sequence. The mixture was heated in a microwave reactor for 30 min at 90 C. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water (and a small amount of brine to break up emulsions, 2x), washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was taken up in MeOH, then loaded onto a 10 g SCX-2 ion exchange column. The column was eluted with MeOH, then with 2M ammonia in MeOH. The basic filtrate was concentrated, and the residue was chromatographed on a 40 g silica gel column with 0 to 10% MeOH/DCM to provide 5-(2-(l -methyl- lH-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-l ,2,3,4- tetrahydroisoquinoline as a pale yellow solid. [M+H]+ = 358.1. XH NMR (400 MHz, DMSO-d6) delta ppm = 7.91 – 7.80 (m, 2 H), 7.56 (d, J= 8.0 Hz, 1 H), 7.28 (d, J= 2.0 Hz, 1 H), 7.09 – 6.95 (m, 2 H), 6.84 (dd, J= 1.3, 7.4 Hz, 1 H), 5.96 (d, J= 1.9 Hz, 1 H), 3.85 (s, 2 H), 3.52 (br. s., 3 H), 2.93 – 2.84 (m, 1 H), 2.79 – 2.67 (m, 1 H), 2.48 – 2.39 (m, 1 H), 2.09 (td, J= 5.3, 16.7 Hz, 1 H)., 923591-51-9
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Reference£º
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem