Lawesson's reagent → HCID 86652847, compound

HRID 1188926Notes

Reaction equation

HRID 1188926 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][N:17]=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:35])=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][N:17]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](=[S:35])[NH2:14])=[CH:8]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66898156HCID 66898156, compound

Product 1

HCID 86652847HCID 86652847, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7-methoxy-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxamide (2.1 g) in tetrahydrofuran (400 mL) was added Lawesson's reagent (2.3 g) and the mixture was stirred at 60° C. for 50 min. The mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. The mixture was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was solidified with ethyl acetate and the resulting solid was washed with diethyl ether to give the title compound (2.06 g, 94%) as a pale yellow solid. MS 378 (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. washthe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-e6a98f3f820d4839b248687e935347de
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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