These common heterocyclic compound, 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine, its 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. Quality Control of N-Boc-2-(4-Bromophenyl)ethylamine
A mixture of N-boc-2-(4-bromophenyl)ethylamine, the desiredarylboronic acid (a-m) (1.2 equiv), tetrakis(triphenylphosphine)-palladium(0) (0.04 equiv), Na2CO3 (5 equiv) in degassed toluene/H2O (5/2) was refluxed for 18 h. The reaction mixture was filteredthrough Celite and concentrated in vacuo. The resulting residuewas dissolved in in EtOAc (200 mL), washed with H2O (200 mL 2) and brine (200 mL). The organic layer was dried with anhydrousNa2SO4 and concentrated in vacuo. The residue was purified by columnchromatography on SiO2. Using Method E, 13 (1.00?g, 3.3?mmol), 4-methoxyphenylboronic acid (0.61?g, 4.0?mmol), tetrakis(triphenylphosphine)palladium(0) (0.15?g, 0.1?mmol), Na2CO3 (1.77?g, 16.7?mmol) in toluene/H2O (33?ml/13.3?ml), followed by 4.0?M HCl in dioxane (2.50?ml, 10.0?mmol) gave 14j as a white solid (0.52?g, 58%): Rf?=?0.00 (EtOAc 9: acetone 1): 1H NMR (DMSO-d6, 400?MHz) delta 3.02-3.05 (m, NH3CH2CH2), 3.82 (OCH3), 6.93 (d, J?=?8.1?Hz, 1 ArH), 7.18-7.23 (m, 2 ArH), 7.35-7.40 (m, 3 ArH), 7.64 (d, J?=?6.8?Hz, 2 ArH), 8.37 (s, NH3); 13C NMR (DMSO-d6, 75?MHz) delta 33.0 (NCH2CH2), 55.6 (CH3), 112.5, 113.4, 119.3, 127.4, 129.7, 130.4, 137.4, 138.9, 141.9, 160.2 (12 ArC).
The synthetic route of N-Boc-2-(4-Bromophenyl)ethylamine has been constantly updated, and we look forward to future research findings.
Reference:
Article; Yeon, Seul Ki; Choi, Ji Won; Park, Jong-Hyun; Lee, Ye Rim; Kim, Hyeon Jeong; Shin, Su Jeong; Jang, Bo Ko; Kim, Siwon; Bahn, Yong-Sun; Han, Gyoonhee; Lee, Yong Sup; Pae, Ae Nim; Park, Ki Duk; Bioorganic and Medicinal Chemistry; vol. 26; 1; (2018); p. 232 – 244;,
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