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

HRID 20991

반응식

HRID 20991 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8021Diethylamine용매

반응 조건

온도
80 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a8a7964606714175a8ec31928416e35e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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