反应详情

温度

-78 °C

To a cold (−78° C.) suspension of 7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (10.38 g, 36.2 mmol) in tetrahydrofuran (80 mL) was added ethynylmagnesium bromide (87 mL, 0.5 M in tetrahydrofuran, 43.4 mmol) dropwise. The reaction mixture was stirred at −78° C. for 1 hour, then at 0° C. for 2 hours. The resultant solution was poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with water and brine and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (4:1 hexanes:ethyl acetate to 7:3 hexanes:ethyl acetate) provided 1-[7-chloro-2-(3-methylphenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-ol (11.3 g, 77%) as a yellow foam. 1H NMR (CDCl3) δ 8.03 (d, 1H), 7.60 (s, 1H), 7.54 (d, 1H), 7.37 (t, 1H), 7.26 (d, 1H), 7.17 (dd, 1H), 6.98 (d, 1H), 2.67 (s, 1H), 2.43 (s, 3H), 2.38 (s, 1H); MS m/z297 (M+1).

1. waitat 0° C. for 2 hours
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with water and brine
4. dry with materialthe combined organics were dried over magnesium sulfate
5. filtrationFiltration and concentration