2-Cyclopenten-1-one → HCID 59326823, compound

HRID 473667Notes

Reaction equation

HRID 473667 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.C1(N(C)C2CCCCC2)CCCCC1.Br[C:22]1[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=1.O1CCOCC1>O>[F:28][C:23]1[C:22]([C:3]2[CH2:4][CH2:5][C:1](=[O:6])[CH:2]=2)=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 135882-Cyclopenten-1-oneHCID 24210N-Methyl dicyclohexylamineHCID 312751,4-DioxaneHCID 27627783-Bromo-2-fluoropyridine

Product 1

HCID 59326823HCID 59326823, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a round bottom flask was added bis(tri-t-butyl)phosphine palladium (0.591 g, 1.156 mmol) before sealing and evacuating and backfilling with nitrogen. Subsequently, cyclopent-2-enone (7.48 mL, 93 mmol), N-cyclohexyl-N-methylcyclohexanamine (14.73 mL, 69.4 mmol), and 3-bromo-2-fluoropyridine (4.07 g, 23.13 mmol) were added before adding dioxane (25 mL). The reaction mixture was stirred under nitrogen at 110° C. for 16 h. The reaction mixture was cooled to room temperature and diluted with water and extracted with ethyl acetate before drying over magnesium sulfate, filtering, and concentrating under reduced pressure. The crude compound was purified by column chromatography (ethyl acetate/dichloromethane) to give 3-(2-fluoropyridin-3-yl)cyclopent-2-enone was afforded as an orange solid. MS (ESI, pos. ion) m/z: 178.0 (M+1).

Workup

  1. customevacuating
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialbefore drying over magnesium sulfate
  5. filtrationfiltering
  6. concentrationconcentrating under reduced pressure
  7. customThe crude compound was purified by column chromatography (ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-5ca7a99e394e4da0a4aeb111f858382b
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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