Water → 3-Amino-6-[1-(tert-butoxycarbonyl)-3-(4-hydroxy-1-butynyl)indol-2-yl]phtalimide

HRID 21107

반응식

HRID 21107 반응식
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:15]3[C:20]([C:21]=2I)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].[CH2:30]([OH:34])[CH2:31][C:32]#[CH:33].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.[Cu](I)I>[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:15]3[C:20]([C:21]=2[C:33]#[C:32][CH2:31][CH2:30][OH:34])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6]

참가 물질

7

반응물 3

HCID 962WaterHCID 135663-Butyn-1-OLHCID 684887473-Amino-6-[1-(tert-butoxycarbonyl)-3-iodoindol-2-yl]phtalimide

생성물 1

HCID 684927783-Amino-6-[1-(tert-butoxycarbonyl)-3-(4-hydroxy-1-butynyl)indol-2-yl]phtalimide수율 87%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8021Diethylamine용매

반응 조건

온도
50 °C

실험 절차

3-Amino-6-[1-(tert-butoxycarbonyl)-3-iodoindol-2-yl]phtalimide (150 mg, 0.298 mmol) was dissolved in diethylamine (7.5 mL), and the solution was added with bis(triphenylphosphine)dichloropalladium (16.7 mg, 0.0234 mmol), copper iodide (11.4 mg, 0.0596 mmol) and 3-butyn-1-ol (0.226 mL, 2.98 mmol), followed by stirring at 50° C. for 3.7 hours under argon atmosphere. 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 and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=10/1) to obtain 3-amino-6-[1-(tert-butoxycarbonyl)-3-(4-hydroxy-1-butynyl)indol-2-yl]phtalimide (115 mg, yield 87%).

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=10/1)

출처 및 근거

ORD 기록
ord-5cb5ea9590ec49be94d9bad2c5ae3039
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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