Dimethyl Sulfide → (3-(Methylthio)-1H-indol-6-yl)(morpholino)methanone

HRID 630440Notes

Reaction equation

[CH3:1][S:2][CH3:3].ClN1C(=O)CCC1=O.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])[CH:19]=2)C=[CH:13]1>ClCCl>[CH3:1][S:2][C:3]1[C:15]2[C:20](=[CH:19][C:18]([C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])=[CH:17][CH:16]=2)[NH:12][CH:13]=1

Participants

Conditions

Temperature: -20 °C

Procedure

Dimethylsulfane (8.17 mL, 109.32 mmol, 1.1 eq) was added dropwise to a stirred suspension of N-chlorosuccinimide (14.53 g, 109.32 mmol, 1.1 eq) in dichloromethane (50 mL) at 0° C. The reaction mixture was cooled to −20° C. and (1H-indol-6-yl)(morpholino)methanone (16.0 g, 99.37 mmol, 1.0 eq) in dichloromethane (120 mL) was added dropwise. After stirring for 1 h at room temperature, the solvent was evaporated and replaced by xylene (100 mL). The mixture was refluxed for 1 h, cooled to ambient temperature and then passed through a silica gel column [100-200 mesh, methanol/dichloromethane=1:19]. The product (16.0 g) obtained was used without further purification.

Workup

customthe solvent was evaporated
temperatureThe mixture was refluxed for 1 h
temperaturecooled to ambient temperature

Sources & evidence

ORD record: ord-f1f9242d834b4f85b14e3d0338e98e46
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315490B2

Reaction notes

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