Trimethylsilylacetylene → Ethyl 2-(4-amino-2-chloro-5-((trimethylsilyl)ethynyl)phenoxy)-4-fluorobenzoate

HRID 624383노트

반응식

HRID 624383 반응식
[NH2:1][C:2]1[C:20](I)=[CH:19][C:5]([O:6][C:7]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([Cl:22])[CH:3]=1.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>C(N(CC)CC)C.C(OCC)(=O)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:20]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[CH:19][C:5]([O:6][C:7]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([Cl:22])[CH:3]=1

참가 물질

7

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 67228200Ethyl 2-(4-amino-2-chloro-5-iodophenoxy)-4-fluorobenzoate

생성물 1

HCID 67226491Ethyl 2-(4-amino-2-chloro-5-((trimethylsilyl)ethynyl)phenoxy)-4-fluorobenzoate

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of EXAMPLE 242B (3.0 g), bis(triphenylphosphine)palladium(II) dichloride (242 mg), CuI (66 mg) in triethylamine (30 mL) was added trimethylsilylacetylene (2.2 g). The mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (200 mL) and washed with aqueous NH4Cl, water, brine and dried over Na2SO4. The mixture was filtered, and the solvent was evaporated and the residue was loaded on a column and eluted with 10% ethyl acetate in hexane to give the pure product.

후처리

  1. washwashed with aqueous NH4Cl, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationThe mixture was filtered
  4. customthe solvent was evaporated
  5. washeluted with 10% ethyl acetate in hexane
  6. customto give the pure product

출처 및 근거

ORD 기록
ord-36193c3b51b848e6a0f41a7f826c2d29
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303025B2

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