Triphenylphosphine Oxide → N-[2-(4,5-dihydro-1,3-thiazol-2-yl)-5-(trifluoromethoxy)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide

HRID 1851564Notes

Reaction equation

HRID 1851564 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.[CH3:36][N:37]([S:77]([C:80]1[S:81][CH:82]=[CH:83][CH:84]=1)(=[O:79])=[O:78])[C:38]1[CH:39]=[C:40]([O:72][C:73]([F:76])([F:75])[F:74])[CH:41]=[C:42]2[C:46]=1[NH:45][C:44]([C:47]([NH:49][CH2:50][CH2:51][S:52]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)=[CH:43]2.C(=O)([O-])O.[Na+]>ClCCl>[S:52]1[CH2:51][CH2:50][N:49]=[C:47]1[C:44]1[NH:45][C:46]2[C:42]([CH:43]=1)=[CH:41][C:40]([O:72][C:73]([F:76])([F:74])[F:75])=[CH:39][C:38]=2[N:37]([CH3:36])[S:77]([C:80]1[S:81][CH:82]=[CH:83][CH:84]=1)(=[O:79])=[O:78]

Participants

6

Reactant 4

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 579017387-[Methyl(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-5-(trifluoromethoxy)-1H-indole-2-carboxamide

Product 1

HCID 11978593N-[2-(4,5-dihydro-1,3-thiazol-2-yl)-5-(trifluoromethoxy)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamideYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of triphenylphosphine oxide (0.37 g), trifluoromethanesulfonic anhydride (0.11 mL), and dichloromethane (5 mL) was stirred for 15 min under ice-cooling. Then, 7-[methyl(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-5-(trifluoromethoxy)-1H-indole-2-carboxamide (0.16 g) was added, and the mixture was stirred for 3 hr under ice-cooling. The reaction solution was poured into aqueous sodium hydrogencarbonate solution and 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=1:4-1:2), and the obtained crystals were washed with diethyl ether-hexane to give the title compound (84 mg, yield 82%) as colorless crystals. melting point 179-180° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3 hr under ice-
  3. temperaturecooling
  4. extractionextracted 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. washthe obtained crystals were washed with diethyl ether-hexane

Sources & evidence

ORD record
ord-61d1b90d22f24ba29e8e34d08c1373b7
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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