tert-butyl (Z)-4-({6-hydroxy-2-[(6-nitro-1H-indol-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate → tert-butyl (Z)-4-({2-[(6-amino-1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate

HRID 1749751노트

반응식

HRID 1749751 반응식
[OH:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6](=[O:22])/[C:7](=[CH:9]/[C:10]3[C:18]4[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=4)[NH:12][CH:11]=3)/[O:8][C:4]=2[C:3]=1[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]1.[H][H]>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[NH2:19][C:15]1[CH:14]=[C:13]2[C:18]([C:10](/[CH:9]=[C:7]3\[O:8][C:4]4[C:3]([CH2:25][N:26]5[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:30][CH2:31]5)=[C:2]([OH:1])[CH:24]=[CH:23][C:5]=4[C:6]\3=[O:22])=[CH:11][NH:12]2)=[CH:17][CH:16]=1

참가 물질

5

반응물 2

HCID 86681943tert-butyl (Z)-4-({6-hydroxy-2-[(6-nitro-1H-indol-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 86681946tert-butyl (Z)-4-({2-[(6-amino-1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate수율 97.7%

시약·촉매·용매 2

HCID 131709914Lindlars catalyst촉매HCID 702Ethanol용매

실험 절차

A solution of tert-butyl (Z)-4-({6-hydroxy-2-[(6-nitro-1H-indol-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.025 g, 0.048 mmol) obtained in Example A24, Step 2 in ethanol (2.0 mL) was added with Lindlar's catalyst (0.010 mg) under an argon atmosphere, and then the inside of the reaction vessel was replaced with hydrogen. The reaction mixture was stirred at room temperature for 5 hours, and then filtered through Celite, and the solvent was evaporated under reduced pressure to obtain tert-butyl (Z)-4-({2-[(6-amino-1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.023 g, 97%).

후처리

  1. filtrationfiltered through Celite
  2. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-26cd767c509140d28b9feca43d536003
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156827B2

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