Triphenylphosphine Oxide → 2-(4,5-Dihydro-thiazol-2-yl)-7-nitro-1H-indole

HRID 1851394Notes

Reaction equation

HRID 1851394 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.[N+:36]([C:39]1[CH:40]=[CH:41][CH:42]=[C:43]2[C:47]=1[NH:46][C:45]([C:48]([NH:50][CH2:51][CH2:52][S:53]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)=[CH:44]2)([O-:38])=[O:37]>ClCCl>[S:53]1[CH2:52][CH2:51][N:50]=[C:48]1[C:45]1[NH:46][C:47]2[C:43]([CH:44]=1)=[CH:42][CH:41]=[CH:40][C:39]=2[N+:36]([O-:38])=[O:37]

Participants

5

Reactant 3

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 579017857-Nitro-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

Product 1

HCID 579015982-(4,5-Dihydro-thiazol-2-yl)-7-nitro-1H-indoleYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of triphenylphosphine oxide (16.7 g) in dichloromethane (30 mL) was slowly added trifluoromethanesulfonic anhydride (5.0 mL) at 0° C., and the mixture was stirred for 10 min and 7-nitro-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (10.1 g) was added. The reaction mixture was stirred at room temperature for 8 hr and concentrated. Saturated aqueous sodium hydrogen carbonate 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 (ethyl acetate:hexane=1:3) to give the title compound (4.0 g, yield 81%) as yellow crystals.

Workup

  1. customat 0° C.
  2. stirringThe reaction mixture was stirred at room temperature for 8 hr
  3. concentrationconcentrated
  4. additionSaturated aqueous sodium hydrogen carbonate was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-be26b043efe54646857063c24c75e3d6
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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