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

HRID 1851477Notes

Reaction equation

HRID 1851477 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][C:37]1[CH:45]=[CH:44][C:43]([NH:46][S:47]([C:50]2[S:51][CH:52]=[CH:53][CH:54]=2)(=[O:49])=[O:48])=[C:42]2[C:38]=1[CH:39]=[C:40]([C:55]([NH:57][CH2:58][CH2:59][S:60]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)[NH:41]2.C(=O)([O-])O.[Na+]>ClCCl>[S:60]1[CH2:59][CH2:58][N:57]=[C:55]1[C:40]1[NH:41][C:42]2[C:38]([CH:39]=1)=[C:37]([CH3:36])[CH:45]=[CH:44][C:43]=2[NH:46][S:47]([C:50]1[S:51][CH:52]=[CH:53][CH:54]=1)(=[O:49])=[O:48]

Participants

6

Reactant 4

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 579016404-Methyl-7-[(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

Product 1

HCID 57901806N-[2-(4,5-dihydro-1,3-thiazol-2-yl)-4-methyl-1H-indol-7-yl]thiophene-2-sulfonamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of triphenylphosphine oxide (2.1 g), trifluoromethanesulfonic anhydride (0.63 mL) and dichloromethane (35 mL) was stirred for 30 min under ice-cooling. 4-Methyl-7-[(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (0.80 g) was added, and the mixture was stirred for 90 min under ice-cooling. The reaction mixture 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=3:7-5:5), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (431 mg, yield 91%) as colorless prism crystals. melting point 198-199° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 90 min 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. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ac44e460f3b6489eb7fad33ab8e7ca8f
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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