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

HRID 1017578Notes

Reaction equation

HRID 1017578 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-ed999bf1bf4f414aad2ebc259f7562a5
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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