2-Pyridinecarboxaldehyde → HCID 58808699, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-ethyl-6-methyl-5-thiophen-2-yl-1H-pyridin-2-one prepared in accordance with the procedures of Example 24, Step 3 (97 mg, 0.442 mmol) in anhydrous THF (1 ml) is cooled to −78° C., and n-BuLi (2.5 M in hexane, 0.4 ml, 1 mmol) is added. The resulting dark green mixture is stirred for 30 min, and then pyridine-2-carbaldehyde (80 mg, 0.746 mmol) is added. The cooling bath is removed after 20 min, and the reaction mixture is slowly warmed to room temperature. After 3 hr, water (5 ml) is added to the mixture, and it is extracted with ethyl acetate. The organic phases are washed and dried, and the residue is purified on silica gel to afford a yellow solid (60 mg). MS: m/e=327 (M+H). 1H-NMR (D6-DMSO, δ ppm) 11.65 (s, 1H); 8.51 (d, 1H); 7.85 (d, 1H); 7.61 (d, 1H); 7.29 (m, 1H); 7.21 (s, 1H); 6.88 (m, 2H); 6.43 (d, 1H); 5.88 (d, 1H); 2.38 (q, 2H); 2.24 (s, 3H); 1.06 (t, 3H, J=7.4 Hz).

Provenance & Evidence