2-Aminopyridine → 2-(2-Benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yloxy)-N-pyridin-2-yl-acetamide

Participants

Reaction Steps

To a solution of compound 22 (100 mg, 0.34 mmol) in THF (5 mL) at room temperature was added HATU (141 mg, 0.37 mmol) and TEA (0.07 mL, 0.48 mmol) and the resulting reaction mixture was stirred at room temperature for 10 minutes. Thereafter 2-aminopyridine (35 mg, 0.37 mmol) was added to the reaction mixture and the resulting reaction mixture was allowed to stir at room temperature for 5 hours. The reaction mixture was poured onto saturated ammonium chloride and extracted with ethyl acetate (3×20 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography (SiO2, 20% EtOAc-Hexanes eluant) provided 80 mg of 23 as a clear oil. (126 mg theoretical, 63% yield). 1H NMR (300 MHz, CDCl3): δ 8.85 (br s, 1H), 8.35 (m, 1H), 8.15 (m, 1H), 7.95 (m, 1H), 7.7 (m, 1H), 7.65-7.45 (m, 2H), 7.45 (m, 2H), 7.3-7.2 (m, 4H), 7.1-7.0 (m, 1H), 5.95 (s, 1H), 5.05 (d, J=15 Hz, 1H), 4.45 (d, J=15 Hz, 1H), 3.65 (d, J=17 Hz, 1H), 3.45 (d, J=17 Hz, 1H). MS (ES) m/z (MH+) 373

Provenance & Evidence