Cyclopropylacetylene → 2-cyclopropyl-1H-indole

HRID 1092413ノート

反応式

HRID 1092413 の反応式
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

参加物

7

反応物 2

HCID 138823CyclopropylacetyleneHCID 1405592'-Iodoacetanilide

生成物 1

HCID 113895272-cyclopropyl-1H-indole

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒2 回HCID 664601,1,3,3-Tetramethylguanidine溶媒2 回

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f0e01993e9cc482989ec6949774b58fd
出典データセット
uspto-grants-2012_03
特許番号
US08129424B2

反応ノート

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