Triethylamine → 3-(2-Trimethylsilylethynylphenyl)urea

HRID 530432노트

반응식

HRID 530432 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH2:11])=[O:10].[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13].C(N(CC)CC)C>CN(C=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>[CH3:15][Si:14]([C:12]#[C:13][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH2:11])=[O:10])([CH3:17])[CH3:16]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 139387Urea, (2-iodophenyl)-

생성물 1

HCID 112992393-(2-Trimethylsilylethynylphenyl)urea수율 90%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

To a degassed solution of 1-(2-iodophenyl)urea (2.62 g, 10 mmol, 1 eq), ethynyltrimethyl silane (4.16 mL, 3 eq), and triethylamine (5.58 mL, 4 eq) in anhydrous DMF (15 mL) was added bis(triphenylphosphine)palladium(II) dichloride (702 mg, 0.1 eq) and copper(I) iodide (190.4 mg, 0.1 eq). After the reaction mixture was stirred at room temperature for 30 minutes, it was partitioned between aqueous ammonium chloride and ethyl acetate. The organic layer was isolated, washed further with saturated sodium bicarbonate, brine, and lastly dried with sodium sulfate. The upper solution was decanted, concentrated, and the brown solid residue was treated with a small amount of DCM. The mixture was stirred at room temperature for 30 minute and filtered to obtain 1-{2-[(trimethylsilyl)ethynyl]phenyl}urea as a white solid in 1.645 g. The filtrate was concentrated and the residue was subject to a gradient column chromatography (EtOAc-hex from 1:100 to 1:1) to render 1-{2-[(trimethylsilyl)ethynyl]phenyl}urea with a second crop of 0.432 g in a total yield of 90%.

후처리

  1. customit was partitioned between aqueous ammonium chloride and ethyl acetate
  2. customThe organic layer was isolated
  3. washwashed further with saturated sodium bicarbonate, brine
  4. dry with materiallastly dried with sodium sulfate
  5. customThe upper solution was decanted
  6. concentrationconcentrated
  7. additionthe brown solid residue was treated with a small amount of DCM
  8. stirringThe mixture was stirred at room temperature for 30 minute
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-318f10ba2c6c40239a0cd76ef4c9f73c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353093B2

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