Cesium carbonate → HCID 11596097, compound

HRID 732139Notes

Reaction equation

HRID 732139 reaction equation
[CH3:1][N:2]1[C:6](S(C)(=O)=O)=[N:5][N:4]=[C:3]1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[O:28][N:27]=[C:26]([CH:29]([OH:31])[CH3:30])[N:25]=2)[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[O:28][N:27]=[C:26]([CH:29]([O:31][C:6]3[N:2]([CH3:1])[C:3]([C:11]4[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=4)=[N:4][N:5]=3)[CH3:30])[N:25]=2)[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 221514774-[5-(Methanesulfonyl)-4-methyl-4H-1,2,4-triazol-3-yl]pyridineHCID 578379411-[5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanol

Product 1

HCID 11596097HCID 11596097, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

1.45 g (6.08 mmol) 4-[4-Methyl-5-(methylsulfonyl)-4H-1,2,4-triazol-3-yl]pyridine, 1.73 g (7.70 mmol) 1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanol and 4.03 g (12.3 mmol) cesium carbonate were dissolved under Ar-atmosphere in DMF (25 mL) and stirred at 30° C. for 3 d. After filtration and evaporation to dryness the crude was purified on 4mm silica chromatotron plate (DCM/MeOH=100/0 to 90/10). Further purification on 2 mm silica chromatotron plate (Hep/EA/MeOH=15/15/1) gave 0.36 g (15%) of the title compound. 1H NMR: 8.75 (br s, 2 H), 8.12 (s, 1 H), 8.00 (d, 1 H), 7.64 (d, 2 H), 7.56 (d, 1 H), 7.46 (t, 1 H), 6.39 (q, 1 H), 3.63 (s, 3 H), 1.94 (d, 3 H).

Workup

  1. filtrationAfter filtration and evaporation to dryness the crude
  2. customwas purified on 4mm silica chromatotron plate (DCM/MeOH=100/0 to 90/10)
  3. customFurther purification on 2 mm silica chromatotron plate (Hep/EA/MeOH=15/15/1)

Sources & evidence

ORD record
ord-e44a1993d3784ba5b1a62b31ffdf9547
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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