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

HRID 1042137Notes

Reaction equation

HRID 1042137 reaction equation
[CH2:1]([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)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>O1CCCC1>[CH2:1]([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)[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 667261757-Ethyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide

Product 1

HCID 866618367-Ethyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carbothioamideYield 131.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-ethyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide (3.4 g), a Lawesson's reagent (2.3 g), and dry tetrahydrofuran (70 mL) was stirred at 55° C. for 3 hr. The reaction solution was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=25:75 to 60:40, volume ratio), and the obtained yellow crystals were washed with ethyl acetate-hexane to give the title compound (2.8 g, yield 79%) as pale-yellow crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. washthe obtained yellow crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-b36b0fec8d364b5bbe6ddfd82b151dc1
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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