Cesium carbonate → HCID 86657446, compound

HRID 1408773Notes

Reaction equation

HRID 1408773 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=O)[NH:14][C:13](=[S:17])[NH:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1.[C:24]([O-:27])([O-])=O.[Cs+].[Cs+].FC(F)(F)S(O[CH2:36][C:37]([F:40])([F:39])[F:38])(=O)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:24](=[O:27])[N:14]([CH2:15][C:37]([F:40])([F:39])[F:38])[C:13]([S:17][CH2:36][C:37]([F:40])([F:39])[F:38])=[N:12]3)[CH2:10][CH:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:8][C:5]2=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 58423943HCID 58423943, compound

Product 1

HCID 86657446HCID 86657446, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-2-phenyl-2′-thioxospiro[chroman-4,4′-imidazolidin]-5′-one (113 mg, 0.29 mmol) in DMF (7 mL) was added Cs2CO3 (190 mg, 0.58 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (204 mg, 0.87 mmol). After stirring for 2 days, the mixture was extracted from water with EtOAc. The combined organic layers were washed with water and brine, dried and then concentrated to give the residue, which was purified by preparative TLC to give 6-bromo-2-phenyl-1′-(2,2,2-trifluoroethyl)-2′-(2,2,2-trifluoroethylthio)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (60 mg, 36%).

Workup

  1. extractionthe mixture was extracted from water with EtOAc
  2. washThe combined organic layers were washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customto give the residue, which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-2a23a5de077445f1a1913d927bec6195
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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