Dimethyl Sulfide → Methyl 3-(methylthio)-1H-indole-6-carboxylate

HRID 630464Notes

Reaction equation

[CH3:1][S:2][CH3:3].ClN1C(=O)CCC1=O.[CH3:12][O:13][C:14]([C:16]1[CH:24]=[C:23]2[C:19](C=[CH:21][NH:22]2)=[CH:18][CH:17]=1)=[O:15]>ClCCl>[CH3:1][S:2][C:3]1[C:19]2[C:23](=[CH:24][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:17][CH:18]=2)[NH:22][CH:21]=1

Participants

Conditions

Temperature: -20 °C

Procedure

Dimethyl sulfide (0.54 mL, 7.42 mmol) was added dropwise at 0° C. to a suspension of N-chlorosuccinimide (0.99 g, 7.42 mmol) in dichloromethane (10 mL). The reaction mixture was cooled to −20° C. and a solution of 1H-indole-6-carboxylic acid methyl ester (1.0 g, 5.71 mmol) in dichloromethane (10 mL) was added. The reaction mixture was warmed to room temperature and stirred for 1 h. The solvent was evaporated and the residue and xylene (50 mL) were refluxed at 140-150° C. for 1 h. The xylene was removed under vacuum and the remnant purified by column chromatography [100-200 mesh silica; dichloromethane/hexane=1:1]. Light brown solid. Yield: 0.9 g (71% of theory). HPLC-MS (method 5): Rt=3.26 min; m/z [M+H]+=222

Workup

temperatureThe reaction mixture was warmed to room temperature
customThe solvent was evaporated
temperaturethe residue and xylene (50 mL) were refluxed at 140-150° C. for 1 h
customThe xylene was removed under vacuum
customthe remnant purified by column chromatography [100-200 mesh silica; dichloromethane/hexane=1:1]

Sources & evidence

ORD record: ord-95fdb5bf24604bbab419b9d88fb0e514
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315490B2

Reaction notes

Loading…