Ethanol → [3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid ethyl ester

HRID 1466807Notes

Reaction equation

HRID 1466807 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:12][C:13]3[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:17][CH:18]=3)=[C:7]([CH3:11])[NH:8]2)=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:28][CH2:29]O>>[CH2:28]([O:21][C:20](=[O:22])[CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([S:12][C:6]2[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]=2[CH3:11])[CH:14]=1)[CH3:29]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 66765068[3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

Product 1

HCID 66765636[3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid ethyl ester

Procedure

[3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid (from the previous step) was dissolved in EtOH (100 mL), conc. H2SO4 (2 mL) was added, and the reaction was stirred at room temperature for 2 hours. The reaction was submitted to standard workup procedures then purified via silica gel chromatography to afford the title compound.

Workup

  1. customthen purified via silica gel chromatography

Sources & evidence

ORD record
ord-dfe6a5076b884ff58bf69f2833bc5e9f
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

Loading…