Acetic Acid → Ethyl 5-[(4-fluorophenyl)methyl]-3-{[3-(methylthio)propyl]amino}-2-pyridinecarboxylate

Participants

Reaction Steps

To a solution of ethyl 3-amino-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (150 mg, 0.547 mmol) in 1,2 dichloroethane (2 mL) was added 3-(methythio)propionaldehyde (82 μL, 0.821 mmol), acetic acid (156 μL, 2.74 mmol), and sodium triacetoxyborohydride (232 mg, 1.09 mmol) respectively. The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane and washed with water and brine, then dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 5%, methanol in dichloromethane) provided ethyl 5-[(4-fluorophenyl)methyl]-3-{[3-(methylthio)propyl]amino}-2-pyridinecarboxylate as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.85 (d, J=1.5 Hz, 1 H), 7.73 (t, J=5.1 Hz, 1 H), 7.11 (dd, J=8.4, 5.5 Hz, 2 H), 6.96 (t, J=8.6 Hz, 2 H), 6.82 (s, 1 H), 4.40 (q, J=7.1 Hz, 2 H), 3.90 (s, 2 H), 3.24 (m, 2 H), 2.58 (m, 2 H), 2.07 (s, 3 H), 1.90 (m, 2 H), 1.41 (t, J=7.1 Hz, 3 H); MS m/z 363 (M+H)+.

Provenance & Evidence