In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 181765-85-5 as follows. Formula: C8H6ClIO2
To a vial was added 1-005(221 mg, 0.506 mmol), methyl 4-chloro-2-iodobenzoate (150 mg, 0.506 mmol) and PdCl2(dppf CH2Cl2 (20.66 mg, 0.025 mmol). THF (3 mL) and 1.5 M Na2CO3 (1.012 mL, 1.518 mmol) were added. The mixture was bubbled with Ar for 3 min. The reaction mixture was sealed and irradiated in a microwave reactor at 100 C for 30 min. The reaction mixture was diluted with EtOAc and 0 and extracted with EtOAc. The combined organic layer was washed with brine, dried with MgS04 and concentrated. The crude residue was purified by ISCO (0-100% EtOAc in Hexanes) to afford the title compound (Example 313a, 160mg, 0.334 mmol, 66.0 % yield). MS (ESI) (m/z) 479 [M + H]+. FontWeight=”Bold” FontSize=”10″ H NMR (500 MHz, CDC13) delta 7.79 – 7.72 (m, 2H), 7.56 (dd, 7=8.0, 0.8 Hz, 1H), 7.38 (dd, 7=8.3, 2.2 Hz, 1H), 7.32 – 7.25 (m, 1H), 7.23 – 7.18 (m, 1H), 7.17 (d, 7=8.3 Hz, 2H), 7.02 (d, 7=8.3 Hz, 2H), 5.68 (s, 2H), 4.15 (q, 7=7.2 Hz, 2H), 3.79 (s, 3H), 3.57 (s, 3H), 1.52 (t, 7=7.0 Hz, 3H).
According to the analysis of related databases, 181765-85-5, the application of this compound in the production field has become more and more popular.
Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com