4-Fluorobenzyl bromide → HCID 57458016, compound

HRID 1787721Notes

Reaction equation

HRID 1787721 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:27][CH2:26][C:20]2([NH:24][NH:23][C:22](=[O:25])[CH2:21]2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CN(C=O)C>[C:10]([O:14][C:15]([N:17]1[CH2:27][CH2:26][C:20]2([N:24]([CH2:6][C:5]3[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=3)[NH:23][C:22](=[O:25])[CH2:21]2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 57426043561314-42-9

Product 1

HCID 57458016HCID 57458016, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Fluorobenzylbromide (0.37 mL, 2.97 mmol) was added dropwise to a solution of 84AF15 (289 mg, 1.13 mmol) in dry DMF (50 mL) at rt. The mixture was stirred at rt for 6 days under argon atmosphere. The solvent was removed by evaporation under reduced pressure and the residue partitioned between chloroform and water. The organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with dichloromethane, afforded the desired compound (160 mg, 39%).

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe residue partitioned between chloroform and water
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by column chromatography on silica gel
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-8c13383252e443d28bfa27d6454508dd
Source dataset
uspto-grants-2009_03
Patent number
US07511053B2

Reaction notes

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