Triphenylphosphine → HCID 67505124、化合物

HRID 1929923ノート

反応式

HRID 1929923 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[CH:2].[CH3:9][O:10][C:11](=[O:26])[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:15](Cl)=[N:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(N(C(C)C)C(C)C)C.[Cu]I>[CH3:9][O:10][C:11](=[O:26])[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:15]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[N:14][CH:13]=1

参加物

7

反応物 3

HCID 11776TriphenylphosphineHCID 137268EthynylpyridineHCID 73013037HCID 73013037、化合物

生成物 1

HCID 67505124HCID 67505124、化合物

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 81531Diisopropylethylamine溶媒2 回

反応条件

温度
120 °C

実験手順

A degassed solution of 2-ethynyl-pyridine (2.0 mmol, CAN 1945-84-2) in tetrahydrofuran and N-ethyldiisopropylamine (1:1, 10 ml) was added to a degassed suspension of 6-chloro-5-(4-chloro-phenyl)-nicotinic acid methyl ester (1.0 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) dichloride dichloromethane complex (1:1) (49 mg, 0.06 mmol), polymer supported triphenylphoshine (135 mg, 1.48 mmol/g, 0.2 mmol) and copper(I)iodide (11 mg, 0.06 mmol) in tetrahydrofuran and N-ethyldiisopropylamine (1:1, 5 ml). The reaction mixture was heated at 120° C. for 20 hours under an atmosphere of nitrogen. The reaction mixture was cooled to room temperature and the solids were removed by filtration. The solids were washed with ethyl acetate (100 ml), the organic liquors were combined and washed with saturated aqueous ammonium chloride solution (3×50 ml). The organic layer was then dried over MgSO4 and concentrated in vacuo. Purification by flash column chromatography (20% ethyl acetate/heptane) gave the title compound as brown oil.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solids were removed by filtration
  3. washThe solids were washed with ethyl acetate (100 ml)
  4. washwashed with saturated aqueous ammonium chloride solution (3×50 ml)
  5. dry with materialThe organic layer was then dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography (20% ethyl acetate/heptane)

出典と根拠

ORDレコード
ord-a66700e5dc6845d99dd6923d1bd440f5
出典データセット
uspto-grants-2012_05
特許番号
US08188093B2

反応ノート

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