Cesium carbonate → HCID 90417507, compound

HRID 633575Notes

Reaction equation

HRID 633575 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[C:10]1[C:18]2[C:13](=[C:14]([O:19][CH3:20])[N:15]=[CH:16][CH:17]=2)[N:12]([CH3:21])[CH:11]=1.[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[OH:30].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[O:30][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[C:10]1[C:18]2[C:13](=[C:14]([O:19][CH3:20])[N:15]=[CH:16][CH:17]=2)[N:12]([CH3:21])[CH:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 90418450HCID 90418450, compound

Product 1

HCID 90417507HCID 90417507, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of Example 95A (3.26 g, 11.47 mmol), 2,4-difluorophenol (1.492 g, 11.47 mmol) and cesium carbonate (4.11 g, 12.61 mmol) in dimethyl sulfoxide (40 mL) was heated at 100° C. for 3 hours. The reaction mixture was partitioned with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride twice, dried with anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 20 to 40% ethyl acetate in heptanes) to provide the title compound (3.98 g, 88%).

Workup

  1. customThe reaction mixture was partitioned with ethyl acetate and water
  2. washThe organic layer was washed with saturated aqueous sodium chloride twice
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel, 20 to 40% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-68281e98f244465bb94d5106e694ba0b
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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