Triphenylphosphine Oxide → HCID 57901662, compound

HRID 1851453Notes

Reaction equation

HRID 1851453 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][C:44]([CH3:68])([CH3:67])[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[S:63][CH:64]=[CH:65][CH:66]=1)(=[O:61])=[O:60])=O)C1C=CC=CC=1>ClCCl>[CH3:67][C:44]1([CH3:68])[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[S:63][CH:64]=[CH:65][CH:66]=2)(=[O:61])=[O:60])=[N:46][CH2:45]1

Participants

5

Reactant 3

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 57901691HCID 57901691, compound

Product 1

HCID 57901662HCID 57901662, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of triphenylphosphine oxide (2.74 g) in dichloromethane (25 mL) was slowly added trifluoromethanesulfonic anhydride (0.83 mL) at 0° C. The mixture was stirred for 10 min, and N-[2-(benzylthio)-2-methylpropyl]-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (0.82 g) was added. The reaction mixture was stirred at room temperature overnight and concentrated. Saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (0.05 g, yield 8%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). melting point 176-177° C.

Workup

  1. customat 0° C
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. concentrationconcentrated
  4. additionSaturated aqueous sodium hydrogen carbonate was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1f88cc79885f47a48e81a4e3a3799f46
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…