Synthetic Route of 13194-68-8, A common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, 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.
To a solution of 4-iodo-2-methyl-aniline (200 mg, 858.19 mumol, 1 eq) and 2-methylpyrazole-3-carboxylic acid (129.87 mg, 1.03 mmol, 1.2 eq) in EtOAc (10 mL) was added T3P (1.64 g, 2.57 mmol, 1.53 mL, 50%, 3.0 eq) and DIEA (332.74 mg, 2.57 mmol, 448.44 muL, 3.0 eq). The mixture was stirred at 60 C. for 3 h. The mixture was stirred at 60 C. for 16 h. The reaction mixture was diluted with NaHCO3 solution (20 mL), extracted with ethyl acetate (20 mL*3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a residue which was purified on silica gel column chromatography (from PE/EtOAc=1/0 to 10/3, TLC: PE/EtOAc=3/1, Rf=0.49) to give the product of N-(4-iodo-2-methyl-phenyl)-2-methyl-pyrazole-3-carboxamide (100 mg, 284.34 mumol, 33.1% yield, 97.0% purity) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.69 (d, J=8.4 Hz, 1H), 7.63-7.56 (m, 2H), 7.53 (d, J=2.2 Hz, 1H), 7.45 (br s, 1H), 6.64 (d, J=2.0 Hz, 1H), 4.23 (s, 3H), 2.28 (s, 3H); ES-LCMS m/z 341.8 [M+H]+.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com