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

HRID 1017578노트

반응식

HRID 1017578 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ed999bf1bf4f414aad2ebc259f7562a5
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479490B2

반응 노트

불러오는 중…