Potassium Carbonate → HCID 90877414, compound

HRID 1455275Notes

Reaction equation

HRID 1455275 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7]([O:11][C:12](=[O:15])[CH2:13]Br)([CH3:10])([CH3:9])[CH3:8].[CH2:16]([C:18]1(OC)[C:22]([O:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)=[CH:21][NH:20][NH:19]1)[CH3:17]>CN(C)C=O>[C:7]([O:11][C:12](=[O:15])[CH2:13][N:19]1[C:18]([CH2:16][CH3:17])=[C:22]([O:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)[C:21]([O:4][CH3:1])=[N:20]1)([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 68951180HCID 68951180, compound

Product 1

HCID 90877414HCID 90877414, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (306 mg, 2.22 mmol) and tert-butylbromoacetate (330 μl, 2.22 mmol) were added to a solution of the benzonitrile of Example 15 (270 mg, 1.11 mmol) in N,N-dimethylformamide (5 ml). The reaction mixture was stirred overnight at 50° C. under nitrogen and then evaporated to dryness. The resulting residue was partitioned between dichloromethane (15 ml) and water (15 ml). The organic layer was separated, and the aqueous layer was extracted twice more with dichloromethane (2×10 ml). The organic extracts were combined, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give a yellow oil. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate:pentane (4:1, by volume) to provide the title compound as a colourless oil (295 mg, 75%).

Workup

  1. customevaporated to dryness
  2. customThe resulting residue was partitioned between dichloromethane (15 ml) and water (15 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice more with dichloromethane (2×10 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow oil
  9. customThe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate:pentane (4:1, by volume)

Sources & evidence

ORD record
ord-d11af1bebb0548929ff379af73a98eb8
Source dataset
uspto-grants-2009_01
Patent number
US07482375B2

Reaction notes

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