Lawesson's reagent → HCID 86652838, compound

HRID 1188895Notes

Reaction equation

[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([NH2:16])=O)=[CH:10]2)[CH3:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>O1CCCC1>[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:17][C:18]2[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:22][CH:23]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14](=[S:37])[NH2:16])=[CH:10]2)[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 7-(1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide (700 mg) in tetrahydrofuran (40 mL) was added Lawesson's reagent (729 mg) and the mixture was stirred at 60° C. for 40 min. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95 to 50/50, volume ratio) to give the title compound (857 mg, 100%) as a yellow amorphous solid. MS 405 (MH+).

Workup

concentrationThe mixture was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95 to 50/50, volume ratio)

Sources & evidence

ORD record: ord-8d5c4c0d0dcc4a299ac6b4a908bf5db4
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673942B2

Reaction notes

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