Lawesson's reagent → HCID 86652849, compound

HRID 1188934Notes

Reaction equation

HRID 1188934 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:17]=[N:18][C:19]([CH2:22][O:23][CH3:24])=[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:34])=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]([CH2:22][O:23][CH3:24])=[CH:20][CH:21]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](=[S:34])[NH2:14])=[CH:8]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66897791HCID 66897791, compound

Product 1

HCID 86652849HCID 86652849, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7-methoxy-5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide (1.86 g) in tetrahydrofuran (40 mL) was added Lawesson's reagent (2.3 g), and the mixture was stirred at 50° C. for 2 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 (ethyl acetate/hexane=30/70 to 90/10, volume ratio) to give the title compound (2.04 g, 100%) as a yellow amorphous solid. MS 344 (MH+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe mixture was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/hexane=30/70 to 90/10, volume ratio)

Sources & evidence

ORD record
ord-eecdcab97a0e4db59d17657f55eb797b
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

Loading…