Cesium carbonate → HCID 86625033, compound

HRID 1686377Notes

Reaction equation

HRID 1686377 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([OH:13])[CH:7]=1)[CH3:2].[CH3:15][S:16]([C:19]1[CH:24]=[CH:23][C:22](F)=[C:21]([Cl:26])[CH:20]=1)(=[O:18])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].CN1C(=O)CCC1>O>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][C:22]2[CH:23]=[CH:24][C:19]([S:16]([CH3:15])(=[O:18])=[O:17])=[CH:20][C:21]=2[Cl:26])[CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 213408802-Chloro-1-fluoro-4-methylsulfonylbenzeneHCID 58785142HCID 58785142, compound

Product 1

HCID 86625033HCID 86625033, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

The product from step (iv) (4.4 g), 3-chloro-4-fluorophenyl methyl sulfone (4.27 g), cesium carbonate (6.5 g) and NMP (40 ml) were charged to a flask and stirred at 90° C. for 2 h. The reaction was diluted with water, extracted with EtOAc, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography (eluent 2:1 isohexane/ether) to give the subtitle compound (3.6 g).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe residue was purified by flash column chromatography (eluent 2:1 isohexane/ether)

Sources & evidence

ORD record
ord-333ab13e856d456ab3ffae2922ee7345
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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