Thioanisole → HCID 57476393, compound

HRID 1960558Notes

Reaction equation

HRID 1960558 reaction equation
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C([S:43][CH:44]([CH:68]([O:71][CH3:72])[O:69][CH3:70])[CH2:45][NH:46][C:47]([C:49]1[NH:50][C:51]2[C:56]([CH:57]=1)=[CH:55][CH:54]=[CH:53][C:52]=2[NH:58][S:59]([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][N:63]=1)(=[O:61])=[O:60])=O)C1C=CC=CC=1.C1(SC)C=CC=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:70][O:69][CH:68]([O:71][CH3:72])[CH:44]1[S:43][C:47]([C:49]2[NH:50][C:51]3[C:56]([CH:57]=2)=[CH:55][CH:54]=[CH:53][C:52]=3[NH:58][S:59]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][N:63]=2)(=[O:61])=[O:60])=[N:46][CH2:45]1

Participants

7

Reactant 5

HCID 7520ThioanisoleHCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 67487159HCID 67487159, compound

Product 1

HCID 57476393HCID 57476393, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triphenylphosphine oxide (849 mg) in dichloromethane (10 mL) was added trifluoromethanesulfonic anhydride (515 μL) under ice-cooling, and the mixture was stirred for 10 min. A solution of N-[2-(benzylthio)-3,3-dimethoxypropyl]-7-[(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxamide (1.5 g) and thioanisole (690 mg) in dichloromethane (10 mL) was added dropwise to the reaction mixture under ice-cooling, and the mixture was stirred for 10 min. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give white crystals from a fraction eluted with ethyl acetate:hexane=50:50. The white crystals were purified by preparative HPLC to give the title compound (487 mg, yield 40%) as white crystals. melting point 153° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 10 min
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give white crystals from a fraction
  9. washeluted with ethyl acetate
  10. customThe white crystals were purified by preparative HPLC

Sources & evidence

ORD record
ord-0a7e0b73156843a1a16adf8b1204e309
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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