Cesium carbonate → HCID 9951410, compound

HRID 1060563Notes

Reaction equation

HRID 1060563 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13](F)[N:12]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[OH:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:18][C:19]4[CH:20]=[CH:21][C:22]([N:25]5[CH:29]=[CH:28][N:27]=[CH:26]5)=[CH:23][CH:24]=4)[N:12]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 823151-(p-Hydroxyphenyl)imidazoleHCID 12042979HCID 12042979, compound

Product 1

HCID 9951410HCID 9951410, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To DMSO (5 mL) was added 2-(1,3-benzodioxol-5-yloxy)-6-fluoropyridine (1.3 g, 5.3 mmol), 1-(4-hydroxyphenyl)imidazole (0.92 mL, 5.8 mmol), and cesium carbonate (1.82 g, 5.6 mmol). After heating at 90° C. for 18 hour, the reaction was partitioned with water and ethyl acetate. The organic layer was washed with water and brine, dried (Na2SO4) and the solvent was removed in vacuo. The residue was chromatographed on silica with ethyl acetate/hexane to get 1.1 g of 2-(1,3-benzodioxol-5-yloxy)-6-[4-(1H-imidazol-1-yl)phenoxy]pyridine; NMR (CDCl3) δ 7.8 (s, 1H), 7.7 (t, 1H), 7.35 (d, 2H), 7.2 (m, 3H), 6.75 (d, 1H), 6.6 (m, 3H), 6.55 (m, 2H), 5.9 (s, 2H) ppm.

Workup

  1. customthe reaction was partitioned with water and ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed in vacuo
  5. customThe residue was chromatographed on silica with ethyl acetate/hexane

Sources & evidence

ORD record
ord-cc5315df5ee4484da2f233ce00ce58b3
Source dataset
uspto-grants-2003_02
Patent number
US06525051B2

Reaction notes

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