Triethylamine → 2-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indole

HRID 1947431ノート

反応式

HRID 1947431 の反応式
I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].C(N(CC)CC)C.[C:23]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)#[CH:24].CCOC(C)=O>CN(C=O)C.[Cu]I.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>[CH:25]1([C:23]2[N:11]([S:12]([CH3:15])(=[O:14])=[O:13])[C:3]3[C:2]([CH:24]=2)=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][CH:4]=3)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 70263EthynylcyclohexaneHCID 67284366N-(2-iodo-4-nitrophenyl)methanesulfonamide

生成物 1

HCID 672853302-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indole収率 91.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a mixture containing N-(2-iodo-4-nitrophenyl)methanesulfonamide (13.5 g; 39.5 mmol), triethylamine (17.9 ml; 129 mmol), ethynylcyclohexane (8.55 g; 79 mmol) in DMF (60 ml), CuI (1.5 g; 7.9 mmol) and dichlorobis(triphenylphosphine)palladium(II) [Cl2(PPh3)2Pd] (2.77 g; 3.95 mmol) were added. The reaction mixture was left under stirring at 70° C. for 18 hours. After cooling to room temperature, EtOAc (100 ml) was added, the inorganic precipitate was filtered off and the solution was transferred into a separating funnel and washed with NaHCO3 (saturated solution, 3×200 ml) and water (2×150 ml). The organic phase was dried over Na2SO4, the solvent was removed by evaporation under reduced pressure. The so obtained crude product was crystallized (isopropylether) to give 2-cyclohexyl-1-(methylsulfonyl)-5-nitro-1H-indole (11.7 g)

後処理

  1. additionwere added
  2. waitThe reaction mixture was left
  3. temperatureAfter cooling to room temperature
  4. filtrationthe inorganic precipitate was filtered off
  5. customthe solution was transferred into a separating funnel
  6. washwashed with NaHCO3 (saturated solution, 3×200 ml) and water (2×150 ml)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. customthe solvent was removed by evaporation under reduced pressure
  9. customThe so obtained crude product
  10. customwas crystallized (isopropylether)

出典と根拠

ORDレコード
ord-61152ca3bce84b399847d4ac6bc6eebb
出典データセット
uspto-grants-2013_03
特許番号
US08399477B2

反応ノート

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