Cesium carbonate → Methyl 5-bromo-6-oxo-1-(3-oxobutan-2-yl)-1,6-dihydropyridine-3-carboxylate

HRID 1909154

Reaction equation

HRID 1909154 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[NH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:20]([CH3:24])[C:21](=[O:23])[CH3:22].C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[Br:11][C:9]1[C:8](=[O:12])[N:7]([CH:20]([C:21](=[O:23])[CH3:22])[CH3:24])[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:10]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 131422-Butanone, 3-bromo-HCID 516892Sodium BicarbonateHCID 2764315Methyl 5-bromo-6-hydroxynicotinate

Product 1

HCID 67338151Methyl 5-bromo-6-oxo-1-(3-oxobutan-2-yl)-1,6-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl-5-bromo-6-oxo-1,6-dihydropyridine-3-carboxylate (10.0 g, 43.1 mmol) and cesium carbonate (16.9 g, 51.7 mmol) in N,N-dimethylformamide (144 mL) was added 3-bromo-2-butanone (7.8 g, 51.7 mmol). The reaction mixture was stirred at ambient temperature. After 20 min, saturated aqueous sodium bicarbonate and water were added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with water (3×), brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→50% dichloromethane/ethyl acetate) gave the title compound. MS 302.1 (M).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×)
  2. washThe combined organic extracts were washed with water (3×), brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% dichloromethane→50% dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-1614fdbe77db41d4bd09d9bb0690ff21
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Linked notes

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