These common heterocyclic compound, 83863-33-6, name is 5-Iodo-2-methylaniline, 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. 83863-33-6
In a 10 mL round-bottomed flask was dissolved 5-iodo-2-methylaniline (5.171 g, 22.19 mmol), 4-(pyridin-2-ylmethoxy)benzoic acid, HCl (4.91 g, 18.49 mmol), DIPEA (9.66 mL, 55.47 mmol) and HATU (14.06 g, 36.98 mmol) in NMP (92 mL) to give an orange solution. The reaction was heated to 70 0C for 12h, after which time, the reaction was poured into IM aqueous NaOH (400 mL), and the resultant precipitate was removed via vacuum filtration. The filter cake was rinsed with water (200 mL), MTBE (100 mL), and dried under suction to yield the title compound (5.52 g, 67%) as a pale brown solid. 1H NMR (DMSO-d6) delta 2.19 (s, 3 H) 5.29 (s, 2 H) 7.08 (d, 1 H) 7.16 (m, 2 H) 7.29 – 7.43 (m, 1 H) 7.50 (dd, 1 H) 7.55 (d, 1 H) 7.73 (d, 1 H) 7.87 (td, 1 H) 7.95 (m, 2 H) 8.61 (d, 1 H) 9.78 (s, 1 H). MS (M+H+) = 445.
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 83863-33-6.
Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/27746; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com