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

HRID 21214

反応式

HRID 21214 の反応式
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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 83717Copper iodide触媒HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

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%).

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=5/1)

出典と根拠

ORDレコード
ord-eea4085c9b7045cbb4b656b9149b9564
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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