Potassium Carbonate → HCID 69023989, compound

HRID 1831907Notes

Reaction equation

HRID 1831907 reaction equation
[Br:1][C:2]1[C:3](=[O:17])[NH:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.[C:18]([O-])([O-])=O.[K+].[K+].[CH:24]1(CBr)[CH2:26][CH2:25]1>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH:24]2[CH2:26][CH2:25]2)[CH:5]=[C:6]([CH3:18])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 22050579HCID 22050579, compound

Product 1

HCID 69023989HCID 69023989, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-bromo-4-(4-fluorobenzyloxy)-1H-pyridin-2-one (0.25 g, 0.84 mmol) in DMF (13 mL) was added K2CO3 (0.33 g, 1.7 mmol) and cyclopropylmethyl bromide (0.14 g, 1.0 mmol), and the reaction mixture was stirred at 110° C. for 2 h. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was diluted with a 50% aqueous solution of brine, and extracted with CHCl3 (3×50 mL). The combined organics were washed with water and then brine, dried (MgSO4), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:1 EtOAc/hexanes) afforded 3-bromo-1-cyclopropyl-methyl-4-(4-fluorobenzyloxy)-1H-pyridin-2-one as a yellow solid (0.12 g, 39%): mp 139-141° C.; 1H NMR (300 MHz, CDCl3) δ 7.43-7.34 (m, 3H), 7.07 (t, J=9 Hz, 2H), 6.06 (d, J=6 Hz, 1H), 5.19 (s, 2H), 3.82 (d, J=9 Hz, 2H), 1.26-1.23 (m, 1H), 0.62-0.57 (m, 2H), 0.40-0.36 (m, 2H). ES HRMS m/z 352.0368 (M+H C16H16BrFNO2 requires 352.0343).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was diluted with a 50% aqueous solution of brine
  4. extractionextracted with CHCl3 (3×50 mL)
  5. washThe combined organics were washed with water
  6. dry with materialbrine, dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash column chromatography (silica, 1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-5bb897014d5b411e8d2f7ee9b582e578
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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