Lawesson's reagent → 7-Methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carbothioamide

HRID 1188911Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([NH2:14])=O)=[CH:8]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](=[S:35])[NH2:14])=[CH:8]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 7-methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide (0.66 g) in tetrahydrofuran (150 mL) was added Lawesson's reagent (0.89 g), and the mixture was stirred at 50° C. for 1 h. Tetrahydrofuran (100 mL) and Lawesson's reagent (0.42 g) were added to the mixture. After stirring at 50° C. for 13 h, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 100/0, volume ratio) to give the title compound (0.68 g, 99%) as a yellow amorphous solid. MS 378 (MH+).

Workup

stirringAfter stirring at 50° C. for 13 h
concentrationthe mixture was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 100/0, volume ratio)

Sources & evidence

ORD record: ord-1688debc50c24cc1b9bef8fca9afe4f2
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673942B2

Reaction notes

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