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

HRID 1851451
Notes
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Reaction equation

HRID 1851451 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.[Cl:36][C:37]1[S:41][C:40]([S:42]([NH:45][C:46]2[CH:47]=[CH:48][CH:49]=[C:50]3[C:54]=2[NH:53][C:52]([C:55]([NH:57][CH2:58][CH2:59][S:60]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=O)=[CH:51]3)(=[O:44])=[O:43])=[CH:39][CH:38]=1>ClCCl>[Cl:36][C:37]1[S:41][C:40]([S:42]([NH:45][C:46]2[CH:47]=[CH:48][CH:49]=[C:50]3[C:54]=2[NH:53][C:52]([C:55]2[S:60][CH2:59][CH2:58][N:57]=2)=[CH:51]3)(=[O:44])=[O:43])=[CH:39][CH:38]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 579017477-{[(5-Chloro-2-thienyl)sulfonyl]amino}-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

Product 1

HCID 579016245-chloro-N-[2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamideYield 37.5%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of triphenylphosphine oxide (3.57 g) in dichloromethane (20 mL) was slowly added trifluoromethanesulfonic anhydride (1.10 mL) at 0° C. The mixture was stirred for 10 min, and 7-{[(5-chloro-2-thienyl)sulfonyl]amino}-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (1.41 g) was added. The reaction mixture was stirred at room temperature for 3 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 and the title compound (0.32 g, yield 37%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:20→1:1, volume ratio). melting point>210° C. (decomposition).

Workup

  1. customat 0° C
  2. stirringThe reaction mixture was stirred at room temperature for 3 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-faa7e714956c4eecb2a05f8bd8ec325b
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957070B2

Reaction notes

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