反应详情

温度

70 °C

Add tin chloride dihydrate (7.13 mg, 31.6 mmol) to a solution of 3-chloro -5-(4-fluoro-3-nitrophenylethynyl)-pyridine, (prepared as described in EXAMPLE 189) (0.97 g, 3.51 mmol) in 2:1 ethanol:tetrahydrofuran (150 mL). Heat the mixture at 70° C. for 2.5 h. Cool to room temperature and concentrate. Dilute with a 50% solution of aqueous potassium hydroxide (300 g) and extract with diethyl ether (5×150 mL). Wash the combined extracts with water (1×50 mL) and saturated aqueous sodium chloride (1×50 mL). Dry (sodium sulfate), filter and concentrate. Purify by silica gel chromatography, eluting with 75:25 hexanes:ethyl acetate, to give the title compound as a light yellow solid (670 mg, 78%).

1. temperatureCool to room temperature
2. concentrationconcentrate
3. additionDilute with a 50% solution of aqueous potassium hydroxide (300 g)
4. extractionextract with diethyl ether (5×150 mL)
5. washWash the combined extracts with water (1×50 mL) and saturated aqueous sodium chloride (1×50 mL)
6. dry with materialDry (sodium sulfate)
7. filtrationfilter
8. concentrationconcentrate
9. customPurify by silica gel chromatography
10. washeluting with 75:25 hexanes