2-Bromopyridine → 3-[2-Methoxy-5-(methylsulfonyl)-3-pyridinyl]-1-(3,4-dichlorophenyl)propan-1-one

HRID 280194ノート

反応式

HRID 280194 の反応式
Br[C:2]1[C:3]([O:12][CH3:13])=[N:4][CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.[CH:14]([CH:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[OH:17])=[CH2:15].C(=O)(O)[O-].[Na+].BrC1C=CC=CN=1>C(OCC)(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].CN(C)C=O>[CH3:13][O:12][C:3]1[C:2]([CH2:15][CH2:14][C:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)=[O:17])=[CH:7][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:5][N:4]=1

参加物

8

反応物 4

HCID 79732-BromopyridineHCID 516892Sodium BicarbonateHCID 135677643-Bromo-2-methoxy-5-(methylsulfonyl)pyridineHCID 135677651-(3,4-Dichlorophenyl)prop-2-en-1-ol

生成物 1

HCID 135677663-[2-Methoxy-5-(methylsulfonyl)-3-pyridinyl]-1-(3,4-dichlorophenyl)propan-1-one

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2.7 g of 3-bromo-2-methoxy-5-(methylsulfonyl)pyridine, 3.1 g of α-ethenyl-3,4-dichlorobenzenemethanol, 1.3 g of sodium bicarbonate, 10 ml of dimethylformamide and 0.11 g of palladium diacetate was stirred under nitrogen and heated to 120° C. After 6 hours, thin layer chromatography showed no unreacted bromopyridine starting material. The mixture was then cooled, diluted with ethyl acetate and filtered through Celite. The ethyl acetate solution was washed with water and then twice with aqueous saturated sodium chloride solution and dried over magnesium sulfate. The solution was then filtered and concentrated to a black oil. Excess alcohol was removed by Kugelrohr distillation and the glassy residue was taken up in methylene chloride and chromatographed on silica gel to give a pale yellow solid. This was recrystallized from ethanol/ethyl acetate to give 3-[2-methoxy-5-(methylsulfonyl)-3-pyridinyl]-1-(3,4-dichlorophenyl)propan-1-one melting at about 145°-146° C.

後処理

  1. temperatureThe mixture was then cooled
  2. filtrationfiltered through Celite
  3. washThe ethyl acetate solution was washed with water
  4. dry with materialtwice with aqueous saturated sodium chloride solution and dried over magnesium sulfate
  5. filtrationThe solution was then filtered
  6. concentrationconcentrated to a black oil
  7. customExcess alcohol was removed by Kugelrohr distillation
  8. customchromatographed on silica gel
  9. customto give a pale yellow solid
  10. customThis was recrystallized from ethanol/ethyl acetate

出典と根拠

ORDレコード
ord-a0dab8627a8e4aac9c45da328017640b
出典データセット
uspto-grants-1986_05
特許番号
US04588733

反応ノート

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