Toluene → 5-(4-chlorophenyl)-N-methoxy-N-methylpyridine-2-carboxamide

HRID 1520293Notes

Reaction equation

HRID 1520293 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])=[N:6][CH:7]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])=[N:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 629527015-Bromo-N-methoxy-N-methylpicolinamide

Product 1

HCID 1178402975-(4-chlorophenyl)-N-methoxy-N-methylpyridine-2-carboxamideYield 39.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

Under a nitrogen atmosphere, a mixture of 5-bromo-N-methoxy-N-methylpyridine-2-carboxamide (2.76 g), 4-chlorophenylboronic acid (2.113 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.920 g), sodium carbonate (3.58 g), toluene (43.3 mL) and water (13 mL) was stirred at 100° C. overnight. To the reaction mixture was added water at room temperature, the mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was fractionated by HPLC(C18, mobile phase: water/acetonitrile (10 mM ammonium hydrogencarbonate-containing system)), the solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.242 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customwater/acetonitrile (10 mM ammonium hydrogencarbonate-containing system)), the solvent was evaporated under reduced pressure
  6. extractionthe residue was extracted with ethyl acetate
  7. washThe extract was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ace7d9666b7c43838eed7b3fe9ee4cff
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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