As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Product Details of 113118-81-3
To a mixture of 5-bromopyridine-3-carbaldehyde (XXXVII) (6.00 g, 32.26 mmol, 1.0 eq), 3,3-difluoropyrrolidine (5.56 g, 38.71 mmol, 1.20 eq) and TEA (5.39 mL, 38.71 mmol, 1.2 eq) in DCE (200 mL) was stirred at room temperature for 30 min, then added sodium triacetoxyborohydride (10.25 g, 48.38 mmol, 1.50 eq) in one portion at room temperature under N2. The mixture was stirred at room temperature for 6 hours. TLC showed the reaction was complete. The reaction was quenched with IN NaOH (100 mL), extracted with DCE (100 mL x 2). The combined organic layers were washed with brine (100 mL), dried and concentrated. The residue was purified by silica gel chromatography (column height: 50 mm, diameter: 50 mm, 300- 400mesh silica gel, DCM/MeOH=30/l?20/l) to give 3-bromo-5-((3,3-difluoropyrrolidin-l- yl)methyl) pyridine (XXXIX): Yellow oil (8.00 g, 28.9 mmol, 89.5% yield). ‘H NMR (CDC13, 400 MHz) delta ppm 2.30 (spt, J=7.2Hz. 2H), 2.75 (t, J=6.8Hz, 2H), 2.91 (t, J=13.2Hz, 2H), 7.85 (s, IH), 8.45 (s, IH), 8.59 (d, J=2Hz, IH); ESIMS found for CioHiiBrF2N2 mlz 277.0 (M+H).
With the rapid development of chemical substances, we look forward to future research findings about 113118-81-3.
Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (299 pag.)WO2017/24015; (2017); A1;,
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