Reference of 202982-67-0,Some common heterocyclic compound, 202982-67-0, name is 4-Chloro-3-fluoroiodobenzene, molecular formula is C6H3ClFI, 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.
A mixture of Example 47C (62 mg, 0.151 mmol), l-chloro-2-fluoro-4-iodobenzene (40.7 mg, 0.159 mmol) and cesium carbonate (148 mg, 0.454 mmol) in dioxane (2.0 mL) was bubbled with argon for 5 minutes and treated with dicyclohexyl(2′,4′,6′-triisopropyl-[l,l’-biphenyl]-2- yl)phosphine (10.82 mg, 0.023 mmol) and Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(O)) (11.08 mg, 0.012 mmol). The reaction mixture was flushed with argon for an additional five minutes and stirred at 95 C for 1 hour. After cooling, the reaction mixture was treated with sodium tetrahydroborate (11.45 mg, 0.303 mmol) and stirred for 2 hours. Volatiles were removed, and the residue was purified by HPLC (20-100% acetonitrile in 0.1% trifluoroacetic acid/water on Phenonemex CI 8 10 muiotaeta column) twice to provide the title compound (33mg, 40%). H NMR (400 MHz, DMSO-d6) delta ppm 7.71 (dd, J = 12.8, 2.5 Hz, 1H), 7.48 (td, J = 8.8, 4.8 Hz, 2H), 7.29 (s, 1H), 7.33 – 7.12 (m, 1H), 7.06 (dd, J = 11.4, 2.9 Hz, 1H), 6.84 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 5.13 (s, 1H), 4.48 (s, 2H), 4.13 – 4.05 (m, 1H), 3.67 (dd, J = 9.2, 6.5 Hz, 2H), 3.45 (dd, J = 9.1, 6.6 Hz, 2H), 2.39 (ddd, J = 12.5, 9.4, 2.5 Hz, 1H), 2.16 – 2.00 (m, 2H), 2.03 – 1.73 (m, 7H); MS (ESI+) m/z 540.2 (M+H)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-fluoroiodobenzene, its application will become more common.
Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; CHUNG, Seungwon; XIONG, Zhaoming; MURAUSKI, Kathleen; ZHANG, Qingwei, I.; BROWN, Brian, S.; DART, Michael, J.; (267 pag.)WO2019/90081; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com