ETHYL 2-(3-AMINOPYRIDIN-2-YL)ACETATE

c) H) Ethyl (3-nitropyridin-2-yl)acetate hydrochloride 24 (401g, 1.63mol, 1.0wt), 10percent palladium on carbon (50g, 12percentw/w) and ethanol (6000mL, 15vol) were charged to a pressure vessel. After purging with nitrogen the reaction mixture was stirred under 3.0 bar hydrogen pressure at 25°C for 18 hours after which TLC analysis (eluent:=tert butyl methyl ether , visualisation: UV), LCMS and 4-Azaoxindole d 1, 3-Dihydro-2H-pyrrolo[3, 2-b]pyridin-2-one d 1, 3-Dihydro-2H-pyrrolo[3, 2-b]pyridin-2-one d) 4-Azaoxindole Under an atmosphere of nitrogen, Pd/C (10%, 1.36 g) was charged to a round bottom flask. Ethyl 2-(3-nitro-pyridin-2-yl)-acetate (8.6 g, 0.41 mol) was dissolved in ethanol (200 mL) and added to the reaction vessel. The reaction was placed under an atmosphere of hydrogen and stirred at room temperature for 30 min. The reaction was filtered through celite and the filtrate was concentrated in vacuo to afford the product as a tan solid (6.94 g, 94% yield).c c Ethyl 2-(3-Amino-pyridin-2-yl)-acetate Under an atmosphere of nitrogen, Pd/C (10%, 1.36 g) was added to a round bottom flask. Ethyl 2-(3-nitro-pyridin-2-yl)-acetate (8.6 g, 0.41 mol) was dissolved in ethanol (200 mL) and added to the reaction vessel. The reaction was placed under an atmosphere of hydrogen and stirred at room temperature for 30 min. The reaction was filtered through celite, and the filtrate was concentrated in vacuo to afford the title compound as a tan solid (6.94 g, 94% yield).c) To a degassed solution of ethyl (3-nitropyridin-2-yl)acetate (3.40 g, 16.2 mmol) in 25 mL of EtOH was added 0.68 g 10% Pd-C. This mixture was hydrogenated at 40 psi for 3.0 h and filtered through celite to give 3.0 g of the title compound after evaporation of solvent: 1H NMR (CDCl3) delta1.21-1.28 (t, 3H), 3.83 (s, 2H), 4.10-4.20 (q, 2H), 6.98-7.04 (m, 2H), 7.98-8.00 (m, 1H). MS: MH+=181.0H) J) ethyl (3-((diethoxyacetyl)amino)pyridin-2-yl)acetate To a solution of

Molecular Weight:180.20
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:180.089877630
Monoisotopic Mass:180.089877630
Topological Polar Surface Area:65.2
Heavy Atom Count:13
Complexity:173
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes