Sodium hydride → HCID 22123282, compound

HRID 1859201

Reaction equation

HRID 1859201 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[C:14](=[O:28])[O:15][C:16](=[O:27])[C:17]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[CH:5]1.Cl[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][Cl:38])[N:32]=1>CN(C)C=O>[Cl:38][CH2:37][C:33]1[N:32]=[C:31]([CH2:30][N:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]([C:17]3[C:16](=[O:27])[O:15][C:14](=[O:28])[C:13]=3[C:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[N:4]([CH3:3])[CH:5]=3)=[CH:19]2)[CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3166542,6-Bis(chloromethyl)pyridineHCID 14855714HCID 14855714, compound

Product 1

HCID 22123282HCID 22123282, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil, 42 mg, 1.8 mmol), 3-(1-methyl-indol-3-yl)-4-(indol-3yl)-furan-2,5-dione (236 mg, 0.7 mmol) and dimethylformamide (8 mL) were stirred at room temperature for 1 h. The reaction mixture was cooled with ice and 2,6-bis-chloromethyl-pyridine (520 mg, 3.0 mmol) was added in one portion. Stirring was continued at room temperature for 65 h. The solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with water, dried with MgSO4, filtered and evaporated. Chromatography (ethyl acetate/heptane:50/50) gave the title compound, which was not pure. Further purification by Kugelrohr distillation (oil pump, 150° C.) afforded 156 mg of the sub-title product.

Workup

  1. additionwas added in one portion
  2. customThe solvent was evaporated
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe organic phase was washed with water
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ba4fd500a14940a49b7e82ea7599e65e
Source dataset
uspto-grants-2000_11
Patent number
US06153641

Linked notes

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