Methyl iodide → Ethyl 7-benzyloxy-4-chloro-1-methyl-2-indolecarboxylate

HRID 564997Notes

Reaction equation

HRID 564997 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:23])=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:26]I>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:23])=[C:13]2[C:17]=1[N:16]([CH3:26])[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21194186Ethyl 7-benzyloxy-4-chloro-2-indolecarboxylate

Product 1

HCID 21194304Ethyl 7-benzyloxy-4-chloro-1-methyl-2-indolecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction was carried out in a manner similar to Reference Example 18 a) except for using 8.00 g (24.3 mmol) of ethyl 7-benzyloxy-4-chloro-2-indolecarboxylate, 0.97 g (24.3 mmol) of 60% sodium hydride, 10.3 g (72.8 mmol) of methyl iodide and 200 ml of dimethylformamide. Ethyl 7-benzyloxy-4-chloro-1-methyl-2-indolecarboxylate was thus obtained in the yield of 7.71 g (92.4%).

Sources & evidence

ORD record
ord-bbda29043f72492082da87ff3f93c0b0
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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