Sodium hydride → 1-[(3-benzyloxyphenyl)methyl]-5-bromo-2-methyl-1H-indole-3-acetic acid ethyl ester

HRID 1901789Notes

Reaction equation

HRID 1901789 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:15])[CH:13]=2)[NH:8][C:7]=1[CH3:16])[CH3:2].[H-].[Na+].[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:15])[CH:13]=2)[N:8]([CH2:31][C:30]2[CH:33]=[CH:34][CH:35]=[C:28]([O:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:29]=2)[C:7]=1[CH3:16])[CH3:2]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 10780239Ethyl 2-(5-bromo-2-methyl-1H-indol-3-yl)acetateHCID 131734903-(Benzyloxy)benzyl chloride

Product 1

HCID 539957391-[(3-benzyloxyphenyl)methyl]-5-bromo-2-methyl-1H-indole-3-acetic acid ethyl esterYield 60.1%

Procedure

1-[(3-Benzyloxyphenyl)methyl]-5-bromo-2-methyl-1-1H-indole-3-acetic acid ethyl ester. Using the procedure described in Example 1, Part F, 592 mg (2 mmol) of 5-bromo-2-methyl-1H-indole-3-acetic acid ethyl ester (Example 51, Part A) was reacted with 80 mg (2 mmol) of 60% NaH/mineral oil and 465 mg (2 mmol) of 3-benzyloxybenzylchloride and after workup of the reaction mixture and chromatograpy on silica(eluted with 33% EtOAc/hexane) there was obtained 592 mg (60%) of 1-[(3-benzyloxyphenyl)methyl]-5-bromo-2-methyl-1H-indole-3-acetic acid ethyl ester as an oil.

Sources & evidence

ORD record
ord-0463e4c911204aabb66ad9a344f86ae0
Source dataset
uspto-grants-1996_11
Patent number
US05578634

Reaction notes

Loading…