反应详情

(0.20 g, 0.96 mmol) (5-Phenylethynyl-pyridin-2-yl)-methanol (example 31, step 1) was dissolved in dichloromethane (5 ml) and methanesulfonyl chloride (75 μl, 0.96 mmol, 1.0 equiv.) and triethylamine (270 μl, 1.91 mmol, 2 equiv.) were added at 0-5° C. The mixture was stirred for 1 hour at room temperature. The reaction mixture was evaporated, dissolved in 2 ml DMF and added to a suspension of morpholin-3-one (97 mg, 0.96 mmol, 1.0 equiv.) previously treated with sodium hydride (60%) (69 mg, 1.43 mmol, 1.5 equiv.) in 2 ml DMF. The mixture was stirred for 3 hours at room temperature. The reaction mixture was treated with sat. NaHCO3 solution and extracted twice with EtOAc. The organic layers were extracted with water, dried over sodium sulfate and evaporated to dryness. The crude material was purified by flash chromatography on silica gel (20 gr, ethyl acetate/heptane gradient, 0:100 to 0:100). The desired 4-(5-phenylethynyl-pyridin-2-ylmethyl)-morpholin-3-one (150 mg, 54% yield) was obtained as a light brown solid, MS: m/e=293.1 (M+H+).

1. customThe reaction mixture was evaporated
2. dissolutiondissolved in 2 ml DMF
3. stirringThe mixture was stirred for 3 hours at room temperature
4. extractionextracted twice with EtOAc
5. extractionThe organic layers were extracted with water
6. dry with materialdried over sodium sulfate
7. customevaporated to dryness
8. customThe crude material was purified by flash chromatography on silica gel (20 gr, ethyl acetate/heptane gradient, 0:100 to 0:100)