Lawesson's reagent → HCID 86652848, compound

HRID 1188930Notes

Reaction equation

HRID 1188930 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH2:29][O:30][CH3:31])[O:5][C:6]1[CH:7]=[C:8]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][N:20]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([NH2:17])=O)=[CH:11]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>O1CCCC1>[CH3:1][O:2][CH2:3][CH:4]([CH2:29][O:30][CH3:31])[O:5][C:6]1[CH:7]=[C:8]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][N:20]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15](=[S:41])[NH2:17])=[CH:11]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagent2×HCID 66897756HCID 66897756, compound

Product 1

HCID 86652848HCID 86652848, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxamide (1.66 g) in tetrahydrofuran (40 mL) was added Lawesson's reagent (1.5 g), and the mixture was stirred at 50° C. for 2 h. Lawesson's reagent (0.5 g) was added to the mixture again. After stirring at 50° C. for 1 h, the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the mixture was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by basic silica gel column chromatography (methanol/ethyl acetate/hexane=0/10/90 to 10/90/0, volume ratio) to give the title compound (1.69 g, 98%) as a yellow amorphous solid. MS 466 (MH+).

Workup

  1. stirringAfter stirring at 50° C. for 1 h
  2. concentrationthe mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe mixture was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by basic silica gel column chromatography (methanol/ethyl acetate/hexane=0/10/90 to 10/90/0, volume ratio)

Sources & evidence

ORD record
ord-68ca239c38c2435a97d86c6444375dcd
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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