6-Ethyl-3-pyridinamine

5-Amino-2-ethylpyridine ; 10percent Palladium-carbon (50percentwet, 90 mg) was added to 5-nitro-2-vinylpyridine (450 mg) in ethanol (30 mL), followed by stirring in a hydrogen atmosphere at room temperature for 15 hours. The catalyst was removed from the reaction mixture by filtration. Subsequently, the solvent was evaporated under reduced pressure, to thereby give the title compound as an oily substance (359 mg, 98percent).1H-NMR(400MHz, CDCl3)δ: 1.25(3H, t, J=7.5Hz), 2.71(2H, q, J=7.5Hz), 3.32-3.78(2H, br), 6.91-6.98(2H, m), 8.02-8.05(1H, m). MS(ESI)m/z: 123(M+H)+.This product was combined with 10% Pd/C (90 mg) and ethanol (20 ml) and was flushed with dry nitrogen. After oxygen exclusion the stirring mix was flushed with H2 and stirred under H2 pressure (balloon) for 16 hours. After this period the reaction mixture was flushed with nitrogen and then filtered through Celite. The filtrate was evaporated in vacuo and purified using flash silica chromatography (0-10% MeOH/DCM w/0.1% diethylamine) to yield 6-ethyl-pyridin-3-ylamine (442 mg, 60%-3 steps) as a brownish residue. 1H-NMR (CDCl3): delta 8.05-8.02 (m, 1H), 6.96-6.93 (m, 2H), 3.55 (br s, 2H), 2.71 (q, J=7.3 Hz, 2H), 1.25 (t, J=7.3 Hz, 3H).A mixture of TEA (0.07 mL, 0.47 mmol), DPPA (0.07 mL, 0.31 mmol), Intermediate 11 (0.1 g, 0.31 mmol) and Inte 108 To a solution of 6-ethylpyridin-3 -amine (500 mg, 4.09 mmol) and formaldehyde (184 mg, 6.14 mmol) in methanol (15 mL) was added sodium methanolate (4.7 mL, 20 mmol) and the reaction mixture was heated at 50 C for 16 h. The reaction mixture was cooled to rt and sodium tetrahydroborate (387 mg, 10.2 mmol) was added in two portions. The reaction mixture was stirred at rt for 2 h, slowly diltued with water (10 mL) and then extracted by EtOAc (2 x 20 mL). The combined organic components were dried with Na2S04, filtered, concentrated and purified with a Biotage Horizon (20-70% EtOAc/Hexane) to afford the title compound (0.41 g) as brown oil. LC-MS retention time = 2.30 min; m/z = 137.05 [M+H] +. (Column: Phenomenex-Luna 2.0 X 50 mm, 3 mupiiota particles; Mobile Phase A: 10% MeOH-90% H2O-0.1% TFA; Mobile Phase B: 90% MeOH-10% H2O-0.1% TFA; Temperature: 40 C; Gradient: 0-100% B over 4 min, then a 1-min hold at 100% B; Flow: 0.8 mL/min; Detection: UV at 220 nm). NMR (400 MHZ, CDCh-d) delta 7.99 (s, 1H), 7.00 (d, J=8.3 Hz, 1H), 6.87 (d, J=11.2 Hz, 1H), 3.65 (br. s, 1H), 2.87 (s, 3H), 2.74 (q, J=7.6 Hz, 2H), 1.29 (t, J=7.6 Hz, 3H).

Molecular Weight:122.17
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:122.084398327
Monoisotopic Mass:122.084398327
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:83
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes