Dimethyl Sulfide → HCID 57503215, compound

HRID 1994899Notes

Reaction equation

HRID 1994899 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]([C:69]#[N:70])[CH2:45][NH:46][C:47]([C:49]1[NH:50][C:51]2[C:56]([CH:57]=1)=[C:55]([CH3:58])[CH:54]=[CH:53][C:52]=2[N:59]([CH3:68])[S:60]([C:63]1[S:64][CH:65]=[CH:66][CH:67]=1)(=[O:62])=[O:61])=O)C1C=CC=CC=1.CSC.C(=O)([O-])O.[Na+]>C(#N)C>[C:69]([CH:44]1[S:43][C:47]([C:49]2[NH:50][C:51]3[C:56]([CH:57]=2)=[C:55]([CH3:58])[CH:54]=[CH:53][C:52]=3[N:59]([CH3:68])[S:60]([C:63]2[S:64][CH:65]=[CH:66][CH:67]=2)(=[O:62])=[O:61])=[N:46][CH2:45]1)#[N:70]

Participants

7

Reactant 5

HCID 1068Dimethyl SulfideHCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 67487301HCID 67487301, compound

Product 1

HCID 57503215HCID 57503215, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of triphenylphosphine oxide (2.35 g) and acetonitrile (20 mL) was slowly added trifluoromethanesulfonic anhydride (0.71 mL) at 0° C., and the mixture was stirred for 10 min. N-[2-(Benzylthio)-2-cyanoethyl]-4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (1.10 g) and dimethylsulfide (0.46 mL) were added. The reaction mixture was stirred at 0° C. for 30 min, saturated aqueous sodium hydrogencarbonate 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 to give the title compound (0.58 g, yield 67%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (3:2, volume ratio). melting point 173-174° C.

Workup

  1. customat 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ec9baf4c806744f79081e6ff548fcfc1
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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