Related Products of 640280-28-0, A common heterocyclic compound, 640280-28-0, name is 1-Bromo-2-iodo-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF3I, 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.
Intermediate J: tert-Butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)-5,6- dihydropyridine- 1 (2H)-carboxylate A solution of l-bromo-2-iodo-4-(trifluoromethyl)benzene (1.408 ml, 8.55 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-5,6- dihydropyridine-l(2H)-carboxylate (Frontier Scientific, Logan, UT, 2.78 g, 8.98 mmol), Pd(dppf)Cl2-CH2Cl2 adduct (Strem Chemicals Inc., Newburyport, MA, 0.349 g, 0.427 mmol), and potassium carbonate (2.052 g, 34.2 mmol) in dioxane (32.1 ml) and water (10.69 ml) was stirred at 70 C for three hours. (LC-MS MH+ 430.1) The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (silica gel 80g, gradient elution 0 to 100% Et20:Heptane) to afford tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine- 1 (2H)- carboxylate (2.54 g, 6.25 mmol) as a light yellow oil. [M+H]+ = 428.0. XH NMR (400 MHz, CHLOROFORM-d) delta ppm = 7.69 (d, J= 8.3 Hz, 1 H), 7.43 (d, J= 2.2 Hz, 1 H), 7.41 – 7.36 (m, 1 H), 5.69 (br. s., 1 H), 4.08 (q, J= 2.7 Hz, 2 H), 3.66 (t, J= 5.6 Hz, 2 H), 2.48 – 2.40 (m, 2 H), 1.52 (s, 9 H)
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com