Triethylamine → 2-Amino-3-cyano-4-methyl-5-[(4-trifluoromethylphenyl)ethynyl]pyridine

HRID 1078243노트

반응식

HRID 1078243 반응식
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11]#[CH:12])=[CH:4][N:3]=1.[F:13][C:14]([F:23])([F:22])[C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1.C(N(CC)CC)C>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11]#[C:12][C:18]2[CH:19]=[CH:20][C:15]([C:14]([F:23])([F:22])[F:13])=[CH:16][CH:17]=2)=[CH:4][N:3]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 233567022-Amino-3-cyano-4-methyl-5-ethynylpyridine

생성물 1

HCID 197072042-Amino-3-cyano-4-methyl-5-[(4-trifluoromethylphenyl)ethynyl]pyridine

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매

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.

후처리

  1. concentrationAfter this time the reaction mixture is concentrated under reduced pressure to a residue
  2. customThe residue is partitioned between ethyl acetate and aqueous 1N hydrochloric acid
  3. customThe aqueous layer and the organic layer are separated
  4. washthe aqueous layer is washed with ethyl acetate
  5. washThe ethyl acetate wash
  6. washthe combination is washed with an aqueous solution of 10% lithium chloride
  7. dry with materialThe organic layer is dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-eab421b86e6145958d18fedb01440436
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05547954

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