Water → 4-(4-Hydroxy-1-butynyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidino methyl)indol-2-yl]isoindolinone

HRID 21214

반응식

HRID 21214 반응식
FC(F)(F)S(O[C:7]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=3)=[C:12]2[C:8]=1[CH2:9][NH:10][C:11]2=[O:39])(=O)=O.[CH2:42]([OH:46])[CH2:43][C:44]#[CH:45].C(N(CC)CC)C.O>C(#N)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[OH:46][CH2:42][CH2:43][C:44]#[C:45][C:7]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([C:32]([O:34][C:35]([CH3:37])([CH3:38])[CH3:36])=[O:33])[C:18]3[C:23]([CH:24]=2)=[CH:22][C:21]([CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=3)=[C:12]2[C:8]=1[CH2:9][NH:10][C:11]2=[O:39]

참가 물질

9

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 866282864-Trifluoromethanesulfonyloxy-7-(1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

생성물 1

HCID 684935994-(4-Hydroxy-1-butynyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidino methyl)indol-2-yl]isoindolinone수율 51.2%

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

4-Trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (80.0 mg, 0.135 mmol) was dissolved in acetonitrile (4.8 mL), and the solution was added with tetrakis(triphenylphosphine)palladium (23.4 mg, 0.0203 mmol), copper iodide (10 mg, 0.054 mmol), tetrabutylammonium chloride (150 mg, 0.405 mmol), 3-butyn-1-ol (0.051 mL, 0.68 mmol) and triethylamine (0.96 mL, 0.70 mmol), followed by stirring at room temperature for 40.7 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=5/1) to obtain 4-(4-hydroxy-1-butynyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidino methyl)indol-2-yl]isoindolinone (35.5 mg, yield 51%).

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=5/1)

출처 및 근거

ORD 기록
ord-eea4085c9b7045cbb4b656b9149b9564
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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