Triphenylphosphine Oxide → HCID 57901847, compound

HRID 1851559Notes

Reaction equation

HRID 1851559 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]([CH3:69])([CH3:68])[CH2:45][NH:46][C:47]([C:49]1[NH:50][C:51]2[C:56]([CH:57]=1)=[CH:55][C:54]([F:58])=[CH:53][C:52]=2[NH:59][S:60]([C:63]1[S:64][CH:65]=[CH:66][CH:67]=1)(=[O:62])=[O:61])=O)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:68][C:44]1([CH3:69])[S:43][C:47]([C:49]2[NH:50][C:51]3[C:56]([CH:57]=2)=[CH:55][C:54]([F:58])=[CH:53][C:52]=3[NH:59][S:60]([C:63]2[S:64][CH:65]=[CH:66][CH:67]=2)(=[O:62])=[O:61])=[N:46][CH2:45]1

Participants

6

Reactant 4

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 57901728HCID 57901728, compound

Product 1

HCID 57901847HCID 57901847, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of triphenylphosphine oxide (0.71 g), trifluoromethanesulfonic anhydride (0.22 mL), and dichloromethane (20 mL) was stirred for 15 min under ice-cooling. Then, N-[2-(benzylthio)-2-methylpropyl]-5-fluoro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (0.23 g) was added, and the mixture was stirred for 5 hr under ice-cooling. The reaction solution was poured into aqueous sodium hydrogencarbonate solution and the mixture was extracted with dichloromethane. The aqueous layer was extracted with dichloromethane, and the combined dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:9-3:7), and the obtained oil was crystallized from diethyl ether-hexane to give the title compound (23 mg, yield 13%) as colorless prism crystals. melting point 175-176° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 5 hr under ice-
  3. temperaturecooling
  4. extractionthe mixture was extracted with dichloromethane
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe combined dichloromethane layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained oil was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-53f92af438614b7688b6376c61f485e4
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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