N-methyl-2-pyrrolidone → HCID 58306560, compound

HRID 1909874Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.CN1CCCC1=O.[CH3:22][S:23]([O-:25])=[O:24].[Na+]>[Cu](Cl)Cl.C(OCC)(=O)C>[CH3:22][S:23]([C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2)(=[O:25])=[O:24]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of methyl 5-bromo-1H-indole-7-carboxylate (300 mg), 1-methyl-2-pyrrolidinone (6 mL), sodium methanesulfinate (600 mg), and copper iodide (I) (1.10 g) was stirred at 150° C. for 17 hours under an argon atmosphere. The reaction mixture was left to be cooled to room temperature, ethyl acetate was added thereto, and then the insoluble materials were removed by filtration. To this filtrate was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 5-(methanesulfonyl)-1H-indole-7-carboxylate (91 mg).

Workup

waitThe reaction mixture was left
temperatureto be cooled to room temperature
customthe insoluble materials were removed by filtration
additionTo this filtrate was added water
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water and saturated brine in this order
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-5d448d9886a243eebe5448ae699c7d18
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598355B2

Reaction notes

Loading…