Triphenylphosphine Oxide → N-methyl-N-[2-(8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide

HRID 504705Notes

Reaction equation

HRID 504705 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]1([CH2:50][NH:51][C:52]([C:54]2[NH:55][C:56]3[C:61]([CH:62]=2)=[CH:60][CH:59]=[CH:58][C:57]=3[N:63]([CH3:72])[S:64]([C:67]2[S:68][CH:69]=[CH:70][CH:71]=2)(=[O:66])=[O:65])=O)[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:72][N:63]([C:57]1[CH:58]=[CH:59][CH:60]=[C:61]2[C:56]=1[NH:55][C:54]([C:52]1[S:43][C:44]3([CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[CH2:50][N:51]=1)=[CH:62]2)[S:64]([C:67]1[S:68][CH:69]=[CH:70][CH:71]=1)(=[O:66])=[O:65]

Participants

6

Reactant 4

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 59135588N-{[4-(benzylthio)tetrahydro-2H-pyran-4-yl]methyl}-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide

Product 1

HCID 24771986N-methyl-N-[2-(8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamideYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of triphenylphosphine oxide (1.15 g) in acetonitrile (20 ml) was slowly added trifluoromethanesulfonic anhydride (0.35 ml) at 0° C., and the mixture was stirred for 10 min. N-{[4-(Benzylthio)tetrahydro-2H-pyran-4-yl]methyl}-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (0.76 g) was added, and the reaction mixture was stirred at 10° C. for 1 hr. 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 (0.22 g, yield 36%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). melting point 189-191° C.

Workup

  1. customat 0° C.
  2. stirringthe reaction mixture was stirred at 10° C. for 1 hr
  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-75a2cc1729d04f67a584ad1040711515
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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