Pyridine → HCID 18469799, compound

Participants

Reaction Steps

To a stirred solution of 5-(2,2,5-trimethyl-1,3-dioxolan-4-yl)-2-pyridinecarboxamide (16.4 mg, 0.0695 mmol) in 1,4-dioxane (1 ml) were added pyridine (23 ml, 0.278 mmol) and trifluoroacetic anhydride (20 ml, 0.139 mmol) at room temperature. After stirring at room temperature for 1 h, the mixture was diluted with ethyl acetate (20 ml), washed with sat. NaHCO3 (10 ml ×2), dried over Na2SO4, and concentrated in vacuo to give a brown syrup. This was purified by preparative TLC [acetone/hexane (1/4, v/v)] to afford 9.7 mg (64%) of 5-(2,2,5-trimethyl-1,3-dioxolan-4-yl)-2-pyridinecarbonitrile as a solid:1H-NMR (270 MHz, CDCl3) δ 8.62 (1H, d, J=1.8 Hz), 7.80 (1H, dd, J=1.8 and 8.1 Hz), 7.70 (1H, d, J=8.1 Hz), 5.25 (1H, d, J=7.0 Hz), 4.67 (1H, quit. J=6.6 Hz), 1.64 and 1.48 (each 3H, 2 s), 0.82 (3 H, d, J=6.6 Hz) ppm.

Provenance & Evidence