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

HRID 565004
Notes
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Reaction equation

HRID 565004 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:23]([F:26])([F:25])[F:24])=[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+].[CH3:29]I>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:23]([F:26])([F:25])[F:24])=[C:13]2[C:17]=1[N:16]([CH3:29])[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
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 211940524-(Trifluoromethyl)-7-(benzyloxy)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 21194661Ethyl 7-benzyloxy-1-methyl-4-trifluoromethyl-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 (22.0 mmol) of ethyl 7-benzyloxy-4-trifluoromethyl-2-indolecarboxylate, 0.88 g (22.0 mmol) of 60% sodium hydride, 6.25 g (44.0 mmol) of methyl iodide and 150 ml of dimethylformamide. Ethyl 7-benzyloxy-1-methyl-4-trifluoromethyl-2-indolecarboxylate was thus obtained in the yield of 7.40 g (89.1%).

Sources & evidence

ORD record
ord-c4fc17d5903a4824b3fdda2a698836bd
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06169107A

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes