反应详情

温度

0 °C

To a solution of 6-iodo-[1,2,4]triazolo[1,5-a]pyridine (5.0 g, 20 mmol; prepared from 2-amino-5-iodopyridine (Aldrich-Sigma, St. Louis, Mo.) according to WO 01/62756) in anhydrous THF (300 mL) at 0° C. was slowly added a solution of isopropylmagnesium bromide in THF (1 M, 31 mL, 31 mmol). The resulting milky suspension was stirred at 0° C. After an hour, DMF (6 mL, 50 mmol) was added to the suspension at 0° C. and the suspension was allowed to warm up to room temperature and stirred for 4 additional hours. 100 mL of water was then added at room temperature and stirred for 1 hour. The resulting mixture was extracted with diethylether and washed with saturated Na2CO3. The extracts were dried over MgSO4 and concentrated. The residue was purified on a short silica gel cake with EtOAc to give [1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde as a light yellow solid (3 g, 100%). ESP+ m/e 148.0. 1H NMR (CDCl3, 300 MHz), δ 10.03 (s, 1H), 9.10 (s, 1H), 8.49 (s, 1H), 8.02 (d, 1H), 7.82 (d, 1H).

1. waitAfter an hour
2. temperatureto warm up to room temperature
3. stirringstirred for 4 additional hours
4. stirringstirred for 1 hour
5. extractionThe resulting mixture was extracted with diethylether
6. washwashed with saturated Na2CO3
7. dry with materialThe extracts were dried over MgSO4
8. concentrationconcentrated
9. customThe residue was purified on a short silica gel cake with EtOAc