The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 872365-91-8, name is 2-Bromo-6-(difluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H4BrF2N
To a stirred solution of 2-bromo-4-fluoropyridine (0.3 g, 1.71 mmol) in 1,4-dioxane (5 mL) was added hexamethylditin (0.43 mL, 2. immol). The reaction mixture was purged with N2 for 10 mm. and to it was added Pd(Ph3P)4 (0.20 g, 0.17 mmol). The reaction mixture was purged once again with N2 for another 10 mm and heated at 110 C for 2 h. Then, after cooling to room temperature, compound 1A (0.43 g, 1.7lmmol) was added and the mixture was purged with N2 for 5 mm., followed by the addition of Pd(Ph3P)4 (0.2 g, 0.17 mmol). The reaction was again heated at 110 C for 18 h. The reaction mixture was concentrated under vacuum to give a crude residue, which was purified by preparative HPLC (Condition N) to provide 6-(4?-fluoro- [2,2?-bipyridinj -3-yl)imidazo [1,2-al pyridine-3 -carbonitrile 16 (0.38 mg, 0.89 mmol, 52.3 % yield). LC-MS: m/z = 317.1 [M+Hf?; ret.time 1.41 mm; condition C. ?H NMR (400 MHz, DMSO-d6) 3 ppm 8.93 – 8.89 (m, 1H), 8.60 – 8.57 (m, 1H), 8.27 – 8.19 (m, 3H), 8.03 – 7.97 (m, 1H), 7.77 – 7.72 (m, 1H), 7.42 – 7.37 (m, 1H), 7.34 – 7.27 (m, 1H). Compound 49 was synthesized by reacting 4 (reference: WO 2015157093 Al and WO 2014055955 Al) and 2-bromo-6-(difluoromethyl)pyridine employing the experimental procedure described in Scheme 4 (Method-D). The crude residue was purified by preparative HPLC (condition-H) to yield 6-(6?-(difluoromethyl)- [2,2?-bipyridinj -3 -yl)imidazo[ 1,2- bjpyridazine-3-carbonitrile 49 (242 mg, 0.0604 mmol, 62.9 % yield). LCMS: m/z = 349.1 [M+Hf?; ret. time 1.53 mm. condition C. ?H NMR (400 MHz, DMSO-d6) oe ppm ppm 8.92 (dd, J4.6, 1.7 Hz, 1H), 8.36 (dd, J8.l, 1.0 Hz, 1H), 8.25 (d, J=9.3 Hz, 1H), 8.21 – 8.18 (m, 2H), 8.16 (t, J=7.8 Hz, 1H), 7.74 (dd, J=7.7, 4.8 Hz, 1H), 7.61 (d, J7.8 Hz, 1H), 7.43 (d, J9.5 Hz, 1H), 6.26 (s, 1H).
With the rapid development of chemical substances, we look forward to future research findings about 872365-91-8.
Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; BRISTOL-MYERS SQUIBB COMPANY; DING, Pingyu; GELMAN, Marina; KINSELLA, Todd; SINGH, Rajinder; BHAMIDIPATI, Somasekhar; VELAPARTHI, Upender; BORZILLERI, Robert, M.; RAHAMAN, Hasibur; WARRIER, Jayakumar, Sankara; (232 pag.)WO2016/133838; (2016); A1;,
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