2-Iodoquinoline → 4-[1,1-Dimethyl-3-(2-quinolyl)-2-propynyloxy]benzonitrile

HRID 1073961

반응식

HRID 1073961 반응식
I[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:12][C:13]([CH3:25])([O:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)[C:14]#[CH:15]>C(NCC)C.[Pd](Cl)Cl.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][C:13]([CH3:25])([O:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=1)[C:14]#[C:15][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

참가 물질

7

반응물 2

HCID 810442-IodoquinolineHCID 27790724-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile

생성물 1

HCID 198956464-[1,1-Dimethyl-3-(2-quinolyl)-2-propynyloxy]benzonitrile수율 93%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 24290Palladium Chloride촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8021Diethylamine용매

실험 절차

5.1 g of 2-iodoquinoline were added at room temperature to a solution of 18 mg of palladium(II) chloride, 52 mg of triphenylphosphine and 38 mg of copper(I) iodide in 100 ml of diethylamine. 3,7 g of 4-(1,1-dimethyl-2-propynyloxy)benzonitrile were added. After stirring at room temperature for 18 hours the mixture was evaporated and the residue was dissolved in ethyl acetate and water. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:2) for the elution to give 5.8 g of 4-[1,1-dimethyl-3-(2-quinolyl)-2-propynyloxy]benzonitrile as a yellow gum.

후처리

  1. customwas evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution

출처 및 근거

ORD 기록
ord-e3e8f97b127644c8963cda6fc5ce7b7b
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04971982

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