Electric Literature of 181765-85-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 181765-85-5, name is Methyl 4-chloro-2-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
A mixture of (2-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3- yl)methyl)pyrimidin-5-yl)boronic acid (Intermediate 188c, 45 mg, 0.145 mmol) and methyl 4-chloro-2-iodobenzoate (40 mg, 0.135 mmol ) in THF (1.5 mL) was treated with 1.5 M Na2C03 (0.270 mL, 0.405 mmol) followed by PdCl2(dppf) (5.51 mg, 6.75 muiotaetaomicron). The resulting mixture was degassed with N2 for 2 min before the reaction vessel was sealed and irradiated in a microwave reactor at 100 C for 30 min. The cooled reaction mixture was diluted with DCM and extracted. The combined organic layer was washed with brine, dried over MgS04, and concentrated to dryness and the residue purified by ISCO (Hexanes/AcOEt, 0-100%) to afford the title compound (Intermediate 198a, 36 mg, 0.083 mmol, 61.2 % yield) as a yellow oil. LC-MS (Method A5): 2.20 min, [M + H]+ = 436.1 ; FontWeight=”Bold” FontSize=”10″ H NMR (500 MHz, CDC13) delta 8.59 (s, 1H), 8.67 – 8.44 (m, 1H), 8.03 (d, 7=8.5 Hz, 1H), 7.52 (dd, 7=8.5, 2.2 Hz, 1H), 6.90 (s, 1H), 5.78 (s, 2H), 3.72 (s, 3H), 2.87 (q, 7=7.7 Hz, 2H), 2.67 (s, 3H), 2.59 (s, 3H), 1.39 (t, 7=7.6 Hz, 3H)
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-chloro-2-iodobenzoate, other downstream synthetic routes, hurry up and to see.
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