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

HRID 1078243ノート

反応式

HRID 1078243 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eab421b86e6145958d18fedb01440436
出典データセット
uspto-grants-1996_08
特許番号
US05547954

反応ノート

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