Synthetic Route of 59786-31-1 ,Some common heterocyclic compound, 59786-31-1, molecular formula is C7H6BrNO2, 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.
PdCl2(PPh3)2 (0.7 g, 1.03 mmol, 0.05 eq.) was added to a solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (6.3 g, 20.5 mmol, 1.0 eq.) in THF (120 mL) under nitrogen. To this was added 3-bromoisonicotinic acid methyl ester (4.4 g, 20.5 mmol, 1.0 eq.). This was followed by the addition of a solution of Na2CO3 (8.7 g, 82.1 mmol, 4.0 eq.) in water (41 mL). The resulting solution was stirred for 14 hours while the temperature was maintained at reflux in an oil bath. The resulting solution was diluted with EtOAc (100 mL), and washed with saturated aqueous NaCl (2*100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:10) to yield 3′,6′-dihydro-2’H-[3,4′]bipyridinyl-4,1′-dicarboxylic acid 1′-t-butyl ester 4-methyl ester (5.6 g) as a yellow oil. H-NMR: (300 MHz, CDCl3, ppm): 8.65 (1H, d, J=4.8 Hz), 8.54 (1H, s), 7.65 (1H, d, J=4.8 Hz), 5.65 (1H, m), 4.08 (2H, m), 3.90 (3H, s), 3.65 (2H, m), 2.34 (2H, m), 1.51 (9H, s).
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. 59786-31-1, Methyl 3-bromoisonicotinate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Stangeland, Eric L.; Patterson, Lori Jean; Zipfel, Sheila; US2011/230495; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem