Sodium hydride → Ethyl 6-(3-tert-butoxycarbonylaminopropoxy)-1-methyl-4-trifluoromethyl-2-indolecarboxylate

HRID 565034Notes

Reaction equation

HRID 565034 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:8]2[CH3:11])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[H-].[Na+].I[CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>CN(C)C=O>[C:30]([O:29][C:28]([NH:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:8]2[CH3:11])=[C:4]([C:17]([F:20])([F:18])[F:19])[CH:3]=1)=[O:34])([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11231463tert-butyl N-(3-iodopropyl)carbamateHCID 22720038Ethyl 6-hydroxy-1-methyl-4-trifluoromethyl-2-indolecarboxylate

Product 1

HCID 21194039Ethyl 6-(3-tert-butoxycarbonylaminopropoxy)-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 5 except for using 1.00 g (3.48 mmol) of ethyl 6-hydroxy-1-methyl-4-trifluoromethyl-2-indolecarboxylate, 0.14 g (3.48 mmol) of 60% sodium hydride, 0.99 g (3.48 mmol) of tert-butyl N-(3-iodopropyl)carbamate and 40 ml of dimethylformamide. Ethyl 6-(3-tert-butoxycarbonylaminopropoxy)-1-methyl-4-trifluoromethyl-2-indolecarboxylate was thus obtained in an amount of 1.28 g.

Sources & evidence

ORD record
ord-dbab989fbe2d49aa81820e26d4f9b289
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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