Reference of 57946-63-1,Some common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.
A round-bottom flask was charged with 2-bromo-4-(trifluoromethyl)aniline (4.115 g, 17.14 mmol), l-methyl-5-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)-lH- pyrazole (4.64 g, 22.29 mmol), potassium phosphate (10.92 g, 51.4 mmol), and Pd(AmPhos)2Ci2 (0.607 g, 0.857 mmol). Dioxane (30 mL) and water (10 mL) were added to give a thick suspension. The flask was fitted with a reflux condenser and placed in a 90 ¡ãC oil bath for 4 h. The mixture was removed from the heat, then diluted with water and extracted with EtOAc (3x). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was partially purified twice by chromatography on silica gel, first with 25 to 75percent EtO Ac/Heptane, then with 20 to70percent EtO Ac/Heptane. The partially purified material thus obtained was dissolved in methanol and loaded onto a lOg SCX-2 ion exchange column. The column was eluted with methanol, then with 2N ammonia in methanol. The basic fractions were combined and concentrated to give 2-(l-methyl-lH-pyrazol-5-yl)-4-(trifluoromethyl)aniline (0.5526 g, 2.291 mmol, 13.36 percent yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) delta = 7.52 (d, J = 1.9 Hz, 1 H), 7.43 (ddd, J = 0.5, 2.3, 8.6 Hz, 1 H), 7.26 (d, J = 1.9 Hz, 1 H), 6.88 (d, J = 8.5 Hz, 1 H), 6.32 (d, J = 1.9 Hz, 1 H), 5.62 (s, 2 H), 3.64 (s, 3 H). m/z (ESI) 242.2 (M+H)+.
The synthetic route of 57946-63-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; DINEEN, Thomas; MARX, Isaac, E.; NGUYEN, Hanh, Nho; WEISS, Matthew; AMGEN INC.; WO2013/25883; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary