p-Fluoronitrobenzene → Ethyl 4-chloro-1-methyl-6-(4-nitrophenoxy)-2-indolecarboxylate

HRID 565047Notes

Reaction equation

HRID 565047 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12].[H-].[Na+].F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 21194263Ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate

Product 1

HCID 21194089Ethyl 4-chloro-1-methyl-6-(4-nitrophenoxy)-2-indolecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction was carried out in a manner similar to Example 186 a) except for using 0.41 g (1.62 mmol) of ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate, 0.09 g (2.23 mmol) of 60% sodium hydride, 0.34 g (2.40 mmol) of 1-fluoro-4-nitrobenzene and 5 ml of dimethylformamide. Ethyl 4-chloro-1-methyl-6-(4-nitrophenoxy)-2-indolecarboxylate was thus obtained in an amount of 0.51 g (92.0%).

Sources & evidence

ORD record
ord-3b08f18307194688843d18cbec01a431
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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