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 1749751ノート

反応式

HRID 1749751 の反応式
[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

参加物

5

反応物 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、化合物

生成物 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-carboxylate収率 97.7%

試薬・触媒・溶媒 2

HCID 131709914Lindlars catalyst触媒HCID 702Ethanol溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-26cd767c509140d28b9feca43d536003
出典データセット
uspto-grants-2015_10
特許番号
US09156827B2

反応ノート

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