Dimethylformamide → HCID 9945584, compound

HRID 2187738Notes

Reaction equation

HRID 2187738 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[CH3:11][O:12][C:13]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[CH:18]2)=[O:14].[H-].[Na+].CN(C)C=O>O>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4][N:20]1[C:21]2[C:17](=[CH:16][C:15]([C:13]([O:12][CH3:11])=[O:14])=[CH:23][CH:22]=2)[CH:18]=[CH:19]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 9945584HCID 9945584, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,4-Dichlorobenzyl chloride (8.68 g) is added to a mixture of 5-methoxycarbonylindole (6.49 g), 60% sodium hydride (2.24 g) and N,N-dimethylformamide, while cooled in an ice-water bath. This is stirred at room temperature for 20 minutes, and water is added thereto. Then, this is extracted with ethyl acetate. After washed with water, the organic layer is dried, concentrated, purified through silica gel column chromatography (eluent: hexane/ethyl acetate=6/1), and finally recrystallized from ethyl acetate/hexane to obtain 1-(2,4-dichlorobenzyl)-5-methoxycarbonylindole (49) (6.59 g).

Workup

  1. temperaturewhile cooled in an ice-water bath
  2. extractionThen, this is extracted with ethyl acetate
  3. washAfter washed with water
  4. customthe organic layer is dried
  5. concentrationconcentrated
  6. custompurified through silica gel column chromatography (eluent: hexane/ethyl acetate=6/1)
  7. customfinally recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ace8d6b55186434ab03c9837545f1243
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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