Sodium hydride → HCID 21194287, compound

HRID 565056Notes

Reaction equation

HRID 565056 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[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].[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19].[H-].[Na+]>CN(C)C=O>[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][O:11][C:8]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]3[C:7]=2[N:6]([CH3:12])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4]3)=[CH:29][CH:28]=1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21194243tert-Butyl 4-(chloromethyl)benzylcarbamateHCID 21194451HCID 21194451, compound

Product 1

HCID 21194287HCID 21194287, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction was carried out in a manner similar to Example 196 a) except for using 0.44 g (1.74 mmol) of ethyl 4-chloro-7-hydroxy-1-methyl-2-indolecarboxylate, 0.66 g (2.58 mmol) of 4-(tert-butoxycarbonylaminomethyl)-benzyl chloride, 0.07 g (1.74 mmol) of 60% sodium hydride and 20 ml of dimethylformamide. Thus, 0.61 g (73.1%) of ethyl 7-[4-(tert-butoxycarbonylaminomethyl)benzyloxy]-4-chloro-1-methyl-2-indolecarboxylate was obtained.

Sources & evidence

ORD record
ord-e5e797b67037425492c0fc152b2f25d0
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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