Ethyl Acetate → HCID 18009120, compound

HRID 987495Notes

Reaction equation

HRID 987495 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9](OS(C)(=O)=O)[CH2:10][CH:11]=[CH2:12])=[CH:5][C:4]=1[F:18])#[N:2].[CH3:19][C:20]1[NH:21][CH:22]=[CH:23][N:24]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:21]2[CH:22]=[CH:23][N:24]=[C:20]2[CH3:19])[CH2:10][CH:11]=[CH2:12])=[CH:5][C:4]=1[F:18])#[N:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 18009113HCID 18009113, compound

Product 1

HCID 18009120HCID 18009120, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the methanesulfonate from Step I (17.3 mmol) in 20 mL of DMF was added 2-methylimidazole (4.25 g, 51.8 mmol) and potassium carbonate (7.15 g, 51.8 mmol). The reaction was heated to 100° C. for 3 hours, then cooled to room temperature. The solution was poured into EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (3-6% MeOH/CH2Cl2) provided the titled compound.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (3-6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2395e122733a42598bf7aab318ba0845
Source dataset
uspto-grants-2003_10
Patent number
US06632818B2

Reaction notes

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