1H-imidazole-2-carbaldehyde → 3-(1-methylindol-3-yl)-4-[3-(imidazol-2-ylmethylamino) phenyl]-1H-pyrrole-2,5-dione

HRID 1017578ノート

反応式

HRID 1017578 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=2)=[CH:3]1.[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O.[BH3-]C#N.[Na+]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH2:30][C:26]3[NH:25][CH:29]=[CH:28][N:27]=3)[CH:17]=2)=[CH:3]1

参加物

5

反応物 3

HCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 5327711Iron oxide, spent

生成物 1

HCID 120181403-(1-methylindol-3-yl)-4-[3-(imidazol-2-ylmethylamino) phenyl]-1H-pyrrole-2,5-dione収率 20%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (100 mg, 0.32 mmol) and imidazole-2-carboxaldehyde (40 mg, 0.42 mmol) in MeOH (8 mL) was stirred for 15 min., and then NaCNBH3 (40.2 mg, 0.64 mmol) was added. After stirring the reaction mixture overnight the volatiles were removed under vacuo and the residue was purified by preparatory TLC (3% MeOH/CH2Cl2) to afford 3-(1-methylindol-3-yl)-4-[3-(imidazol-2-ylmethylamino)phenyl]-1H-pyrrole-2,5-dione (24.8 mg, 20 %). LC/MS: M+ 397(94.2%).

後処理

  1. stirringAfter stirring the reaction mixture overnight the volatiles
  2. customwere removed under vacuo
  3. customthe residue was purified by preparatory TLC (3% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-ed999bf1bf4f414aad2ebc259f7562a5
出典データセット
uspto-grants-2002_11
特許番号
US06479490B2

反応ノート

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