Tetrahydro-4H-pyran-4-one → 3-(1-methylindol-3-yl)-4-(3-tetrahydropyran-4-ylaminophenyl)-1H-pyrrole-2,5-dione

HRID 1017576Notes

Reaction equation

HRID 1017576 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.[O:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1.[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][CH:28]3[CH2:29][CH2:30][O:25][CH2:26][CH2:27]3)[CH:17]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 5003444Sodium cyanoborohydrideHCID 5327711Iron oxide, spent

Product 1

HCID 120181393-(1-methylindol-3-yl)-4-(3-tetrahydropyran-4-ylaminophenyl)-1H-pyrrole-2,5-dioneYield 70%

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 tetrahydro-4H-pyran-4-one (65 mg, 0.65 mmol) in MeOH (8 mL) was stirred at room temperature for 40 min., and then NaCNBH3 (63 mg, 1.0 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 give 3-(1-methylindol-3-yl)-4-(3-tetrahydropyran-4-ylaminophenyl)-1H-pyrrole-2,5-dione (88.2 mg, 70%). LC/MS: M+ 401(98.6%).

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-8fa03dfec6434a34aedf7cc9e3667cee
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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