3-Fluoro-N-methoxy-N-methylpicolinamide → [4-(Benzyloxy)phenyl](3-fluoropyridin-2-yl)methanone

HRID 573349Notes

Reaction equation

HRID 573349 reaction equation
[F:1][C:2]1[C:3]([C:8](N(OC)C)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:8]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=2)=[O:9])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 866889893-Fluoro-N-methoxy-N-methylpicolinamideHCID 178419638HCID 178419638, compound

Product 1

HCID 86688990[4-(Benzyloxy)phenyl](3-fluoropyridin-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide (4.8 g) in THF (100 mL) was added dropwise [4-(benzyloxy)phenyl]magnesium bromide (1 M solution in THF, 27.4 mL) at 0° C. After stirring at 0° C. for 2 h, the mixture was warmed to room temperature and stirred at room temperature overnight. The mixture was quenched with water and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (3.0 g).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred at room temperature overnight
  3. customThe mixture was quenched with water
  4. extractionextracted with AcOEt
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-d857cec3c5e345ac95eab4b94aef57b1
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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