Benzyl Bromide → HCID 22319086, compound

HRID 2356900Notes

Reaction equation

HRID 2356900 reaction equation
[Br:1][C:2]1[C:3](=[O:20])[N:4]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[Br:1][C:2]1[C:3](=[O:20])[N:4]([C:14]2[CH2:15][N:16]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:18][CH:19]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 7498Benzyl Bromide2×HCID 22318994HCID 22318994, compound

Product 1

HCID 22319086HCID 22319086, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

718 mg of 3-bromo-5-(2-pyridyl)-1-(3-pyridyl)-1,2-dihydropyridin-2-one was dissolved in 40 ml of acetonitrile. 383 mg of benzyl bromide was added thereto, followed by stirring at 70° C. overnight. Further, 383 mg of benzyl bromide was added thereto, followed by stirring at 70° C. for 2 nights. After cooling to room temperature, the mixture was evaporated. The residue was dissolved in 30 ml of methanol, followed by cooling to 0° C. under stirring. 265 mg of sodium borohydride was added thereto, followed by stirring overnight under heating from 0° C. to room temperature. Water was added thereto, the solvent was evaporated, and then the residue was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 550 mg of 3-bromo-5-(2-pyridyl)-1-(1-benzyl-1,2,5,6-tetrahydropyridin-3-yl)-1,2-dihydropyridin-2-one. 270 mg of the product was dissolved in 20 ml of dimethylformamide. 179 mg of 2-(2-cyanophenyl)-1,3,2-dioxaborinate, 313 mg of cesium carbonate and 15 mg of tetrakistriphenylphosphine palladium were added thereto, followed by stirring at 120° C. for 1 hour. After cooling to room temperature, water was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 174 mg of the title compound.

Workup

  1. stirringby stirring at 70° C. for 2 nights
  2. temperatureAfter cooling to room temperature
  3. customthe mixture was evaporated
  4. dissolutionThe residue was dissolved in 30 ml of methanol
  5. temperatureby cooling to 0° C.
  6. stirringunder stirring
  7. addition265 mg of sodium borohydride was added
  8. stirringby stirring overnight
  9. temperatureunder heating from 0° C. to room temperature
  10. additionWater was added
  11. customthe solvent was evaporated
  12. extractionthe residue was extracted with ethyl acetate
  13. washThe organic layer was washed with brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customThe solvent was evaporated
  16. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-805e7f638e6e426093d9162286911033
Source dataset
uspto-grants-2010_07
Patent number
US07759367B2

Reaction notes

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