Related Products of 660-49-1, A common heterocyclic compound, 660-49-1, name is 3-Fluoro-5-iodoaniline, molecular formula is C6H5FIN, 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.
A solution of 3-fluoro-5-iodoaniline (250 mg, 1.055 mmol) and dihydro-2H- pyran-4(3H)-one (264 mg, 2.637 mmol) in methanol (5 mL) was charged into a 25 mL round bottom flask with a magnetic stir bar. Acetic acid (0.121 mL, 2.11 mmol) was added and the resulting solution was stirred for 30 minutes at room temperature. Sodium cyanoborohydride (133 mg, 2.11 mmol) was added, the resulting solution was stirred overnight at room temperature. The reaction was quenched with 10 mL 1M aqueous NaOH, stirred for 15 minutes. The solution was extracted with EtOAc (3 x 15 mL), the combined organic layers were washed with brine (15 mL), dried with MgS04, filtered, and evaporated under vaccuum. The crude product was dry loaded onto 3 g. silica and purified by column chromatography (ISCO normal phase, 24 g. gold column, 0-60% EtOAc/hexanes gradient) to isolate N-(3-fluoro-5-iodophenyl)tetrahydro-2H-pyran-4- amine (047) (208 mg, 0.648 mmol, 61%). 1H NMR (400 MHz, CDCb) d ppm 1.41 – 1.55 (m, 2 H) 1.95 – 2.09 (m, 2 H) 3.38 – 3.48 (m, 1 H) 3.53 (td, 7=11.61, 2.13 Hz, 2 H) 3.65 – 3.80 (m, 1 H) 4.02 (br d, 7=11.54 Hz, 2 H) 6.20 – 6.30 (m, 1 H) 6.73 (br d, 7=1.76 Hz, 2 H). LCMS: 322.6 [M+H]+.
The synthetic route of 660-49-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; COOK, Andrew; REYNOLDS, Dominic; ZHONG, Cheng; BRAWN, Ryan; ELLERY, Shelby; SAMARAKOON, Thiwanka; LIU, Xiang; PRAJAPATI, Sudeep; SHEEHAN, Megan; LOWE, Jason T.; PALACINO, James; (378 pag.)WO2019/200100; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com