Cesium carbonate → 3-(2-Fluoro-4-nitrophenoxy)-2,6-dimethyl-pyridine

HRID 404703

Reaction equation

HRID 404703 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1F>CN(C=O)C>[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1[O:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 707322,6-Dimethyl-3-pyridinolHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 592873193-(2-Fluoro-4-nitrophenoxy)-2,6-dimethyl-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

2,6-Dimethyl-pyridin-3-ol (3.0 g, 24.35 mmol) and cesium carbonate (15.87 g, 48.71 mmol) were added to a solution of 3,4-difluoronitrobenzene (3.87 g, 24.35 mmol) in DMF (30 ml). The mixture was heated at 140° C. for 2 hours. After cooling to room temperature it was filtered through diatomaceous earth and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; 2% methanol/DCM as eluent) to yield intermediate D14 (5.88 g, 92%).

Workup

  1. temperatureAfter cooling to room temperature it
  2. filtrationwas filtered through diatomaceous earth
  3. customthe solvent evaporated in vacuo
  4. customThe crude product was purified by column chromatography (silica gel; 2% methanol/DCM as eluent)
  5. customto yield intermediate D14 (5.88 g, 92%)

Sources & evidence

ORD record
ord-d4df6e9c113040a08a2f20ae8c1a501d
Source dataset
uspto-grants-2014_06
Patent number
US08748621B2

Linked notes

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