Water → 1-(Tert-butoxycarbonyl)-5-(3-dimethylamino-2-propyn-1-yl)indole

HRID 20991

反応式

HRID 20991 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](I)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]([CH3:23])[CH2:20][C:21]#[CH:22].O>C(NCC)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>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:22][C:21]#[C:20][N:19]([CH3:23])[CH3:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 962WaterHCID 81643N,N-DimethylpropargylamineHCID 161259585-Iodo-1H-indole, N-BOC protected

生成物 1

HCID 684934291-(Tert-butoxycarbonyl)-5-(3-dimethylamino-2-propyn-1-yl)indole収率 90%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8021Diethylamine溶媒

反応条件

温度
80 °C

実験手順

1-(tert-Butoxycarbonyl)-5-iodoindole (1.00 g, 2.91 mmol) was dissolved in diethylamine (20 mL), and the solution was added with bis(triphenylphosphine)dichloropalladium (163 mg, 0.233 mmol), cuprous iodide (44.4 mg, 0.233 mmol) and 1-dimethylamino-2-propyne (0.628 mL, 5.82 mmol), followed by stirring at 80° C. for 7.0 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography (chloroform/methanol=19/1) to obtain 1-(tert-butoxycarbonyl)-5-(3-dimethylamino-2-propyn-1-yl)indole (0.78 g, yield 90%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by preparative thin-layer chromatography (chloroform/methanol=19/1)

出典と根拠

ORDレコード
ord-a8a7964606714175a8ec31928416e35e
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

関連ノート

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