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

HRID 1909154

反応式

HRID 1909154 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1614fdbe77db41d4bd09d9bb0690ff21
出典データセット
uspto-grants-2013_12
特許番号
US08598209B2

関連ノート

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