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

HRID 1909154

반응식

HRID 1909154 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1614fdbe77db41d4bd09d9bb0690ff21
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598209B2

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