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 139585-70-9, name is 6-Bromonicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromonicotinonitrile
lOld (59 mg, 0.19 mmol), 2-bromo-5-cyanopyridine (52 mg, 0.28 mmol), trans- dichlorobis(triphenylphosphine)palladium (II) (14 mg, 0.02 mmol), and copper(I) iodide (6 mg, 0.03 mmol) were mixed in a round bottom flask and placed under a nitrogen atmosphere. THF (1 mL) and triethylamine (0.053 mL, 0.380 mmol) were added, and the reaction mixture was stirred at 60 C for 1.5 hours. The reaction mixture was cooled to room temperature and diluted with EtOAc. The mixture was washed with sat’d aqueous NH4CI followed by brine, dried over MgSO/i, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0 to 50% EtOAc in heptane) gave 6-((3-((lS,5S,6S)-3-amino-l,5- bis(fluoromethyl)-2-thia-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4- fluorophenyl)ethynyl)nicotinonitrile (101, 33 mg, 0.08 mmol, 42% yield) as an off-white solid. LC/MS (ESI+) m/z = 413.1 [M+H]+. NMR (400 MHz, DMSO-d6) delta ppm 9.05 (d, J = 1.37 Hz, 1H) 8.38 (dd, J = 8.22, 2.15 Hz, 1H) 7.96 (dd, J = 7.63, 2.15 Hz, lH) 7.85 (d, J = 8.22 Hz, 1H) 7.67 (ddd, J = 8.31, 4.50, 2.25 Hz, 1H) 7.35 (dd, J = 11.93, 8.41 Hz, 1H) 6.54 (s, 2H) 4.58 – 4.77 (m, 2H) 4.38 – 4.58 (m, 2H) 1.85 (t, J = 8.12 Hz, 1H) 1.19 (dd, J = 9.68, 5.38 Hz, 1H) 0.58 – 0.64 (m, 1H).
With the rapid development of chemical substances, we look forward to future research findings about 139585-70-9.
Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; CHEN, Jian J.; FROHN, Michael J.; HARRINGTON, Paul E.; LOW, Jonathan D.; MA, Vu V.; NGUYEN, Thomas T.; PICKRELL, Alexander J.; REEVES, Corey; (122 pag.)WO2018/112086; (2018); A1;,
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