(1-Bromoethyl)benzene → HCID 66765564, compound

HRID 1466790Notes

Reaction equation

HRID 1466790 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.[H-].[Na+].Br[CH:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:27]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]([CH:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH3:27])[C:12]=2[CH3:21])[CH:5]=1

Participants

5

Reactant 3

HCID 11454(1-Bromoethyl)benzeneHCID 24758Sodium hydrideHCID 66765016HCID 66765016, compound

Product 1

HCID 66765564HCID 66765564, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(6-chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.100 g, 0.30 mmol) was dissolved in DMF (3 mL) then sodium hydride (60% dispersion in mineral oil, 0.015 g, 0.36 mmol) was added followed by (1-bromoethyl)benzene (0.045 mL, 0.33 mmol). After 1 hour, the reaction was quenched with HCl (1N), followed by standard workup. Silica gel chromatography yielded the title compound.

Workup

  1. customthe reaction was quenched with HCl (1N)

Sources & evidence

ORD record
ord-cfa32ff5923941ab92450d2ec6d63ae0
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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