Water → N-(2,6-dichloro-5-fluoro-pyridin-3-ylmethyl)-N-(2-vinyl-phenyl)-acetamide

HRID 2224299Notes

Reaction equation

HRID 2224299 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:11])=[N:5][C:6]([Cl:10])=[C:7]([F:9])[CH:8]=1.[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:23])[CH3:22])=[CH2:13].[H-].[Na+].O>CN(C=O)C>[Cl:11][C:4]1[C:3]([CH2:2][N:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:12]=[CH2:13])[C:21](=[O:23])[CH3:22])=[CH:8][C:7]([F:9])=[C:6]([Cl:10])[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12464032N-(2-Ethenylphenyl)acetamideHCID 597175733-(Bromomethyl)-2,6-dichloro-5-fluoropyridine

Product 1

HCID 59717570N-(2,6-dichloro-5-fluoro-pyridin-3-ylmethyl)-N-(2-vinyl-phenyl)-acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 1B (0.5 g, 1.93 mmol) and N-(2-vinyl-phenyl)-acetamide bb (0.314 g, 1.95 mmol) in DMF (5 mL) was added NaH (47 mg, 1.95 mmol) at 0° C. The reaction mixture was stirred for 30 minutes at room temperature, then poured into H2O (50 mL) and extracted with Et2O (20 mL). The Et2O layer was washed with H2O (2×20 mL), dried (MgSO4), filtered and concentrated in vacuo to give 1C (0.63 g, 96%). HPLC Rt=3.212 min. (Column: YMC ODS-A 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA).

Workup

  1. extractionextracted with Et2O (20 mL)
  2. washThe Et2O layer was washed with H2O (2×20 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-785737f82afe4b12b86355e8e4348efe
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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