Cesium carbonate → HCID 18194855, compound

HRID 2377806Notes

Reaction equation

HRID 2377806 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=1>CN(C=O)C>[N+:23]([C:22]1[C:17]([O:9][C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]#[N:2])=[N:18][CH:19]=[CH:20][CH:21]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 133943-CyanophenolHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 18194855HCID 18194855, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

3-cyanophenol (187 mg, 1.06 mmol) was dissolved in DMF (1 mL) and cesium carbonate (360 mg, 1.1 mmol) was added followed by a solution of 2-chloro-3-nitropyridine (158 mg, 1.0 mmol) in DMF (1 mL). The reaction mixture was heated with shaking at 80° C. for 18 h. The mixture was concentrated. The residue was dissolved in ethyl acetate (4 mL) and washed with water (0.6 mL), saturated NaHCO3 (0.5 mL) and water (2×0.5 mL). The organic phase was concentrated and the resulted mixture containing mainly 106a was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. concentrationThe mixture was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (4 mL)
  4. washwashed with water (0.6 mL), saturated NaHCO3 (0.5 mL) and water (2×0.5 mL)
  5. concentrationThe organic phase was concentrated
  6. additionthe resulted mixture containing mainly 106a
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-dceab323fd1e40929df0a79f468c4881
Source dataset
uspto-grants-2008_12
Patent number
US07470712B2

Reaction notes

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