반응 #320792

반응 방정식

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

4-trifluoromethylphenyl iodide

triethylamine

→

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

용매

acetonitrile

반응 조건

후처리

1. 1
   농축After this time the reaction mixture is concentrated under reduced pressure to a residue
2. 2
   기타The residue is partitioned between ethyl acetate and aqueous 1N hydrochloric acid
3. 3
   기타The aqueous layer and the organic layer are separated
4. 4
   세척the aqueous layer is washed with ethyl acetate
5. 5
   세척The ethyl acetate wash
6. 6
   세척the combination is washed with an aqueous solution of 10% lithium chloride
7. 7
   건조The organic layer is dried with magnesium sulfate
8. 8
   여과filtered
9. 9
   농축The filtrate is concentrated under reduced pressure

실험 절차

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.

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