Electric Literature of 1133879-69-2 ,Some common heterocyclic compound, 1133879-69-2, molecular formula is C7H6FN, 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.
Tetra butyl ammonium bromide (7 mg, 0.023 mmol) was dissolved in 50% aqueous sodium hydroxide and stirred for 10 min. at RT. Carboline 1 (0.1 g, 0.47 mmol) was added to the reaction mixture and stirred for 10 min. at RT. 3-Fluoro-5-vinylpyridine (69 mg, 0.56 mmol) was added, and the reaction mixture stirred at 100 C overnight. The reaction was monitored by TLC and LCMS. Upon completion of reaction, the mixture was cooled to RT and the compound was extracted with EtOAc twice. The combined organic layers were dried over anhydrous sodium sulfate and concentrated to yield the crude product, which was purified by reverse phase chromatography to give 15 mg of product as TFA salt.[0353] Analytical HPLC: YMC ODS A, 4.6 x 150 mm, 5 jim, mobile phase A: 0.05% TFA, mobile phase B: 0.05% TFA in Acetonitrile, gradient, 5% to 95% B in 8 min., hold for 1.5 min., 95% to 5% B in 0.01 min., retention time (min.), 5.51, purity, 95.02%, flow rate, 1.4 mL/min. 1H NMR (DMSO, TFA salt) d (ppm) 10.9-10.8 (m, 1H), 8.50-8.45 (m, 1H), 8.15-8.10 (m, 1H), 7.65-7.55 (m, 1H), 7.40-7.30 (m, 2H), 7.05-6.90 (m, 1H), 4.75-4.65 (m, 2H), 4.40-4.20 (m, 2H), 3.95-3.40 (m, 2H), 3.35-3.15 (m, 1H), 3.10-3.00 (m, 2H), 2.44-2.25 (m, 5H), 2.15-2.00 (m, 2H). H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1133879-69-2, 3-Fluoro-5-vinylpyridine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; JAIN, Rajendra, Parasmal; CHAKRAVARTY, Sarvajit; WO2011/38163; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem