Triphenylphosphine Oxide → HCID 59135950, compound

HRID 504876Notes

Reaction equation

HRID 504876 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]([CH2:69][N:70]1[CH2:75][CH2:74][S:73](=[O:77])(=[O:76])[CH2:72][CH2:71]1)[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[N:58]([CH3:68])[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>ClCCl.C(OCC)(=O)C>[O:77]=[S:73]1(=[O:76])[CH2:72][CH2:71][N:70]([CH2:69][CH:44]2[S:43][C:47]([C:49]3[NH:50][C:51]4[C:56]([CH:57]=3)=[CH:55][CH:54]=[CH:53][C:52]=4[N:58]([CH3:68])[S:59]([C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][N:63]=3)(=[O:60])=[O:61])=[N:46][CH2:45]2)[CH2:75][CH2:74]1

Participants

6

Reactant 3

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 59135918HCID 59135918, compound

Product 1

HCID 59135950HCID 59135950, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of triphenylphosphine oxide (0.50 g) in dichloromethane (5 mL) was slowly added trifluoromethanesulfonic anhydride (0.25 mL) under ice-cooling, and the mixture was stirred for 20 min. A solution of N-[2-(benzylthio)-3-(1,1-dioxidothiomorpholino)propyl]-7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxamide (0.37 g) in dichloromethane (5 mL) was added dropwise, and the mixture was stirred for 30 min under ice-cooling. The reaction solution was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=3:7-10:0). The obtained colorless oil was crystallized from ethyl acetate-hexane to give the title compound (87 mg, yield: 28%) as colorless prism crystals. MS: 520 (MH+). melting point 188-189° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 min under ice-
  3. temperaturecooling
  4. washwashed with aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained colorless oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a84ae4a4e8eb44f39439528cff236242
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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