Pyridine → HCID 23370191, compound

HRID 741840Notes

Reaction equation

HRID 741840 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].N1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17]1(C)[CH:22]=CC(S(Cl)(=O)=O)=C[CH:18]=1.[NH4+].[Cl-]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8]([C:13]([C:14]3[CH:22]=[CH:17][CH:18]=[CH:16][CH:15]=3)=[CH:12][N:7]=[CH:6]2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 211563-MethoxybenzylamineHCID 25517Ammonium Chloride

Product 1

HCID 23370191HCID 23370191, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxybenzylamine (15 g) and pyridine (15 mL) in CH2Cl2 (100 mL) at 0° C. was added p-toluenesulfonyl chloride (21 g) portionwise. After addition was complete, the mixture was stirred at r.t. for 2 h and then saturated NH4Cl was added. The mixture was extracted with Et2O and the extracts were washed with H2O, brine, dried (MgSO4) and concentrated. The residue, 2-bromoacetophenone (23 g) and Cs2CO3 (45 g) in acetone (400 mL) were stirred at r.t. for 20 h. The acetone was evaporated and saturated NH4Cl was added. The mixture was extracted with EtOAc and the organics were washed with H2O, brine, dried (MgSO4) and concentrated. The residual solid was swished in Et2O for 3 h and then mixed with TFA (17 mL). After heating at 75° C. for 2.5 h, the mixture was cooled to r.t., EtOAc and H2O were added and the aqueous phase was made basic by the careful addition of solid K2CO3. The organic phase was washed with saturated NaHCO3, H2O, brine and dried (MgSO4). Concentration and chromatography (silica gel; hexane/EtOAc (3:2 to 1:1) provided the title compound as a solid.

Workup

  1. additionAfter addition
  2. extractionThe mixture was extracted with Et2O
  3. washthe extracts were washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. stirringThe residue, 2-bromoacetophenone (23 g) and Cs2CO3 (45 g) in acetone (400 mL) were stirred at r.t. for 20 h
  7. customThe acetone was evaporated
  8. additionsaturated NH4Cl was added
  9. extractionThe mixture was extracted with EtOAc
  10. washthe organics were washed with H2O, brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated
  13. waitThe residual solid was swished in Et2O for 3 h
  14. additionmixed with TFA (17 mL)
  15. temperatureAfter heating at 75° C. for 2.5 h
  16. temperaturethe mixture was cooled to r.t.
  17. additionEtOAc and H2O were added
  18. additionthe aqueous phase was made basic by the careful addition of solid K2CO3
  19. washThe organic phase was washed with saturated NaHCO3, H2O, brine
  20. dry with materialdried (MgSO4)
  21. concentrationConcentration and chromatography (silica gel

Sources & evidence

ORD record
ord-2586889655484078a90602357eba02b2
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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