反应 #320792

反应方程式

2-amino-3-cyano-4-methyl-5-ethynylpyridine

4-trifluoromethylphenyl iodide

triethylamine

→

2-amino-3-cyano-4-methyl-5-[(4-trifluoromethylphenyl)ethynyl]pyridine

溶剂

acetonitrile

反应条件

后处理

1. 1
   浓缩After this time the reaction mixture is concentrated under reduced pressure to a residue
2. 2
   其他The residue is partitioned between ethyl acetate and aqueous 1N hydrochloric acid
3. 3
   其他The aqueous layer and the organic layer are separated
4. 4
   洗涤the aqueous layer is washed with ethyl acetate
5. 5
   洗涤The ethyl acetate wash
6. 6
   洗涤the combination is washed with an aqueous solution of 10% lithium chloride
7. 7
   干燥The organic layer is dried with magnesium sulfate
8. 8
   过滤filtered
9. 9
   浓缩The filtrate is concentrated under reduced pressure

实验过程

A solution of 1.6 grams (0.010 mole) of 2-amino-3-cyano-4-methyl-5-ethynylpyridine, 3.8 grams (0.014 mole) of 4-trifluoromethylphenyl iodide (commercially available), 3.5 grams (0.035 mole) of triethylamine, 0.3 gram (catalyst) of bis(triphenylphosphine)palladium(II) chloride, and 0.3 gram (catalyst) of copper(I) iodide in 75 mL of acetonitrile is stirred at ambient temperature for about 18 hours. After this time the reaction mixture is concentrated under reduced pressure to a residue. The residue is partitioned between ethyl acetate and aqueous 1N hydrochloric acid. The aqueous layer and the organic layer are separated, and the aqueous layer is washed with ethyl acetate. The ethyl acetate wash is combined with the organic layer, and the combination is washed with an aqueous solution of 10% lithium chloride. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 2-amino-3-cyano-4-methyl-5-[(4-trifluoromethylphenyl)ethynyl]pyridine.

来源