Cesium carbonate → HCID 18194855, compound

HRID 555403Notes

Reaction equation

HRID 555403 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-46fcd2b033b64ac581923bc75fa0717d
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

Loading…