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

HRID 1042143Notes

Reaction equation

HRID 1042143 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:14][C:15]2[CH:16]=[N:17][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:19][CH:20]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([NH2:13])=O)=[CH:7]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([O:14][C:15]2[CH:16]=[N:17][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:19][CH:20]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11](=[S:34])[NH2:13])=[CH:7]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 667261417-Methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide

Product 1

HCID 866618387-Methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carbothioamideYield 138.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide (2.95 g), a Lawesson's reagent (2.1 g), and dry tetrahydrofuran (70 mL) was stirred at 55° C. for 2 hr. The reaction solution was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=40:60 to 55:45, volume ratio). The obtained yellow oil was crystallized from ethyl acetate-hexane to give the title compound (2.6 g, yield 84%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe obtained yellow oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8df18488abe345c3922374db7eca59fe
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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