Application of 64115-88-4,Some common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, molecular formula is C7H4BrF3O, 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.
General procedure: To a microwave vial with stir bar was added 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(3,4,5-trimethoxyphenyl)benzo[d]oxazol-2-amine (97 mg, 0.228 mmol), 4-bromo-1H-benzo[d]imidazole (30 mg, 0.152 mmol), DME (1.5 mL), Sodium carbonate (0.76 mL, 1.523 mmol) [2.0M (aq)] and PdCl2(dppf)-CH2Cl2 adduct (12.43 mg, 0.015 mmol). Vial capped and heated in an aluminum tray at 120 C for 3 hr. Reaction mixture was cooled to RT, diluted with water. Aqueous mixture was extracted with EtOAc. Organic phases combined, washed with brine, dried (Na2SO4), filtered and concentrated. Residue dissolved with DMSO and purified by RHPLC. Product fractions combined, frozen and lyophilized to afford a TFA salt of 7-(1H-benzo[d]imidazol-4-yl)-N-(3,4,5-trimethoxyphenyl) benzo[d]oxazol-2-amine (8.1 mg, 0.015 mmol, 9.93 % yield).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-(trifluoromethoxy)benzene, its application will become more common.
Reference:
Article; Costales, Abran; Mathur, Michelle; Ramurthy, Savithri; Lan, Jiong; Subramanian, Sharadha; Jain, Rama; Atallah, Gordana; Setti, Lina; Lindvall, Mika; Appleton, Brent A.; Ornelas, Elizabeth; Feucht, Paul; Warne, Bob; Doyle, Laura; Basham, Stephen E.; Aronchik, Ida; Jefferson, Anne B.; Shafer, Cynthia M.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1592 – 1596;,
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