Hydroxyacetone → HCID 12018145, compound

HRID 1017582Notes

Reaction equation

HRID 1017582 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.[OH:25][CH2:26][C:27](=O)[CH3:28].[BH3-]C#N.[Na+]>C(Cl)Cl.C1COCC1>[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:27]([CH3:28])[CH2:26][OH:25])[CH:17]=2)=[CH:3]1

Participants

6

Reactant 3

HCID 8299HydroxyacetoneHCID 5003444Sodium cyanoborohydrideHCID 5327711Iron oxide, spent

Product 1

HCID 12018145HCID 12018145, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (100 mg, 0.32 mmol) and hydroxyacetone (0.03 mL, 1.5 eq) in CH2Cl2 (12 mL) and THF (5 mL) was added NaCNBH3 (28 mg, 1.5 eq) and the reaction mixture was stirred overnight. The volatiles were removed under vacuo and the residue was purified by preparatory TLC to give 3-(1-methylindol-3-yl)-4-[3-(2-hydroxy-1-methylethylamino)phenyl]-1H-pyrrole-2,5-dione (8 mg). LC/MS: M+ 375(85.6%).

Workup

  1. customThe volatiles were removed under vacuo
  2. customthe residue was purified by preparatory TLC

Sources & evidence

ORD record
ord-9eded9c2607949d39b951ae7dce278f7
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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