Cesium carbonate → HCID 24853175, compound

HRID 500554Notes

Reaction equation

HRID 500554 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C@H:13]([OH:15])[CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.CS([C:20]1[N:21]([CH3:33])[C:22]([C:25]2[CH:30]=[CH:29][N:28]([CH3:31])[C:27](=[O:32])[CH:26]=2)=[N:23][N:24]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C@H:13]([O:15][C:20]3[N:21]([CH3:33])[C:22]([C:25]4[CH:30]=[CH:29][N:28]([CH3:31])[C:27](=[O:32])[CH:26]=4)=[N:23][N:24]=3)[CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 24851817HCID 24851817, compoundHCID 46701926(R)-1-[5-(3-chloro-phenyl)-isoxazol-3-yl]-ethanol

Product 1

HCID 24853175HCID 24853175, compound

Conditions

Temperature
60 °C

Procedure

The title compound from example 17.1 (96 mg, 0.43 mmol), the title compound from example 34.1 (100 mg, 0.36 mmol) and cesium carbonate (419 mg, 1.29 mmol) were combined with a stir bar in a screw cap vial which was purged with nitrogen. The combined reagents were stirred in DMF and heated to 60° C. overnight. The reaction mixture was then diluted with water and extracted three times with chloroform. The organic phase was dried over magnesium sulfate, filtered and concentrated then chromatographed in 0-10% methanol in ethyl acetate (pale solid, 105 mg, 68%).

Workup

  1. customcap
  2. customwhich was purged with nitrogen
  3. additionThe reaction mixture was then diluted with water
  4. extractionextracted three times with chloroform
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthen chromatographed in 0-10% methanol in ethyl acetate (pale solid, 105 mg, 68%)

Sources & evidence

ORD record
ord-3483fdf48446459e96d70a0770189613
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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