Reference of 887266-99-1,Some common heterocyclic compound, 887266-99-1, name is 3-Fluoro-4-iodobenzonitrile, molecular formula is C7H3FIN, 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.
To a mixture of tert- butyl (S)-7,l0-dioxo-6-(4-(trifluoromethyl)benzyl)-2,6,9- triazaspiro[4.5]decane-2-carboxylate (280 mg, 0.63 mmol), Cul (60 mg, 0.32 mmol, 0.5 equiv.), K2CO3 (349 mg, 2.53 mmol, 4.0 equiv.) and aryl iodide (234 mg, 0.95 mmol, 1.5 equiv.) in l,4-dioxane (6 mL) was added N,N-dimethylethylenediamine (0.034 mL, 0.32 mmol, 0.5 equiv.). The resulting mixture was heated at 115 C under N2 for 18 h in a sealed tube, cooled to r.t, filtered through celite, washed with additional dioxane (15 mL) and DCM (30 mL), concentrated under reduced pressure, and purified by silica gel chromatography using EA / Hex (1/1) as eluents to provide 187 mg (54%) of tert-butyl (S)-9-(4-cyano-2- fluorophenyl)-7,l0-dioxo-6-(4-(trifluoromethyl)benzyl)-2,6,9-triazaspiro[4.5]decane-2- carboxylate. LRMS (APCI) m/z 491.1 (M+H) (-C4H9). NMR (400 MHz, Methanol-i/4) d 7.82 – 7.64 (m, 5H), 7.50 (d, J = 8.0 Hz, 2H), 5.15 – 5.02 (m, 1H), 4.81 – 4.57 (m, 3H), 4.00 (d, J = 12.1 Hz, 1H), 3.66 (d, J = 12.3 Hz, 1H), 3.62 – 3.47 (m, 2H), 2.59 – 2.48 (m, 2H),
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Fluoro-4-iodobenzonitrile, its application will become more common.
Reference:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; ASHCRAFT, Luke W.; LAU, Kevin; (455 pag.)WO2020/47447; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com