Cyclopropylacetylene → 2-cyclopropyl-1H-indole

HRID 1092413노트

반응식

HRID 1092413 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[CH3:10].[CH:12]1(C#C)[CH2:14][CH2:13]1>O1CCOCC1.CN(C)C(N(C)C)=N.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>[CH:12]1([C:9]2[NH:8][C:3]3[C:4]([CH:10]=2)=[CH:5][CH:6]=[CH:7][CH:2]=3)[CH2:14][CH2:13]1

참가 물질

7

반응물 2

HCID 138823CyclopropylacetyleneHCID 1405592'-Iodoacetanilide

생성물 1

HCID 113895272-cyclopropyl-1H-indole

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매2회HCID 664601,1,3,3-Tetramethylguanidine용매2회

반응 조건

온도
80 °C

실험 절차

To a solution of N-(2-iodophenyl)acetamide (100 mg, 0.38 mmol) in dioxane (750 mL) and 1,1,3,3-tetramethylguanidine (750 mL) was added cyclopropylacetylene (41 mL, 0.49 mmol), bis(triphenylphosphine)palladium(II) chloride (35 mg, 0.05 mmol), and copper(I) iodide (10 mg, 0.05 mmol). The reaction was stirred overnight at 80° C. The solution was cooled and partitioned between water and methylene chloride. The organic layer was dried (MgSO4) and concentrated to give the uncyclized Sonagashira coupling product. Dioxane (750 mL) and 1,1,3,3-tetramethylguanidine (750 mL) were added and the reaction was stirred overnight at 90° C. The solution was again partitioned between water and methylene chloride. The organic layer was dried (MgSO4) and concentrated to give the desired indole, which was used without further purification.

후처리

  1. temperatureThe solution was cooled
  2. custompartitioned between water and methylene chloride
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customto give the uncyclized Sonagashira coupling product
  6. stirringthe reaction was stirred overnight at 90° C
  7. customThe solution was again partitioned between water and methylene chloride
  8. dry with materialThe organic layer was dried (MgSO4)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f0e01993e9cc482989ec6949774b58fd
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129424B2

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