Synthetic Route of 1072448-08-8 , The common heterocyclic compound, 1072448-08-8, name is Methyl 3-amino-5-bromopicolinate, molecular formula is C7H7BrN2O2, 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.
Step 3: methyl 3-amino-5-(benzylsulfanyl)pyridine-2-carboxylate: [00313] A flask containing methyl 3-amino-5-bromopyridine-2-carboxylate (826 mg, 3.57 mmol, Step 2), benzylthiol (630 muL, 5.37 mmol) and DBU (1.6 mL, 10.7 mmol) mixed with N- methylmorpholine (8 mL) was flushed with nitrogen, and the reaction mixture heated at reflux for 40 minutes, with brisk stirring as a second phase forms, then brought to room temperature. The mixture was partially concentrated, treated with 1 M aqueous citric acid (7 mL) and extracted four times with 1:1 CH2Cl2/heptane. The combined organic phases were washed with 1:11 M aqueous citric acid/brine, and the separated aqueous phase was extracted once with 1:1 CH2Cl2/heptane. The organic phases were dried (Na2SO4), combined and filtered with a thorough CH2Cl2 rinse of the solids. The filtrate was concentrated and chromatographed on silica (0 to 10% ethyl acetate in 1:1 CH2Cl2/heptanes) to give the titled compound (518 mg). 1H NMR (500 MHz, DMSO-d6) delta ppm 3.77 (s, 3H), 4.30 (s, 2H), 6.70 (s, 2H), 7.14 (d, J = 2.0 Hz, 1H), 7.24 – 7.28 (m, 1H), 7.31 – 7.35 (m, 2H), 7.40 – 7.43 (m, 2H), 7.73 (d, J = 2.0 Hz, 1H); MS (DCI) m/z 275 (M+H)+.
The synthetic route of 1072448-08-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ABBVIE S.A.R.L.; GALAPAGOS NV; ALTENBACH, Robert, J.; COWART, Marlon, D.; DE MUNCK, Tom, Roger Lisette; DROPSIT MONTOVERT, Sebastien Jean, Jacques Cedric; GFESSER, Gregory, A.; KELGTERMANS, Hans; MARTINA, Sebastien, Laurent Xavier; VAN DER PLAS, Steven, Emiel; WANG, Xueqing; (300 pag.)WO2016/193812; (2016); A1;,
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