3'-Nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid, 98+% C11H13N3O4, MW: 251.24 synthesis

Yield:758720-54-6 82%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in 1-methyl-pyrrolidin-2-one at 120; for 1.5 h;Microwave irradiation;Inert atmosphere;

Steps:

15) 1-(3-nitropyridin-2-yl)piperidine-4-carboxylic acid (24B)

To a solution of piperidine-4-carboxylic acid (2.0 g, 15.0 mmol) in NMP (6 ml) was added 2-chloro-3-nitropyridine (2.41 g, 15.0 mmol), followed by diisopropyl ethylamine (7.9 ml, 45.1mmol). The mixture was heated in a microwave oven at 120°C for 90 minutes. The reactionmixture was poured onto water and extracted with ethyl acetate. The organic phase was washedwith brine and dried over sodium sulfate. The solution was filtered and concentrated. Columnchromatography on silica (ethyl acetate/heptane) provided 3.1 g (11.1 mmol, 82%) of 1-(3-nitropyridin-2-yl)piperidine-4-carboxylic acid.

References:

Schlapbach, Achim;Revesz, Laszlo;Pissot Soldermann, Carole;Zoller, Thomas;Régnier, Catherine H.;Bornancin, Frédéric;Radimerski, Thomas;Blank, Jutta;Schuffenhauer, Ansgar;Renatus, Martin;Erbel, Paulus;Melkko, Samu;Heng, Richard;Simic, Oliver;Endres, Ralf;Wartmann, Markus;Quancard, Jean [Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,# 12,p. 2153 - 2158] Location in patent:supporting information