2-Aminopyridine → HCID 21193119, compound

Participants

Reaction Steps

To a solution of 160 mg of 2-bromo-1-(1-benzoyl-4-piperidyl)-1-ethanone (prepared in analogy with Example 523, Step A) in 6 mL ethanol was added 59 mg of 2-aminopyridine. After refluxing for 18 hours, the solvent was evaporated. The mixture was partitioned between EtOAc and saturated sodium bicarbonate solution. Aqueous layer was extracted with EtOAc (3×). The combined organic phase was washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography with 100% EtOAc followed by 10% MeOH in EtOAc to give 78 mg of a solid: 1H NMR (500 MHz, CDCl3) δ1.80 (d, 2H), 2.16 (d, 2H), 3.17 (m, 3H), 3.87 (br, 1H), 4.85 (br, 1H), 6.76 (t, J=6.8 Hz,1H). 7.15 (m,1H), 7.37(s, 1H), 7.42(m, 5H), 7. 55(d, J=9.1 Hz, 1H), 8.08 (d, J=6.9 Hz,1H).

Provenance & Evidence