Dimethylformamide → 5-Bromo-4-propylpicolinonitrile

HRID 1038548ノート

反応式

HRID 1038548 の反応式
Br[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[C:5]([Br:11])=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].[CH3:17][N:18](C)C=O>>[Br:11][C:5]1[C:6]([CH2:8][CH2:9][CH3:10])=[CH:7][C:2]([C:17]#[N:18])=[N:3][CH:4]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 866471942,5-Dibromo-4-propylpyridine

生成物 1

HCID 665981895-Bromo-4-propylpicolinonitrile収率 60%

反応条件

温度
100 °C

実験手順

To a solution of 2,5-dibromo-4-propylpyridine (100 mg, 0.444 mmol) in N,N-dimethylformamide (0.9 mL), dinitrile zinc (57 mg, 0.449 mmol) and tetrakistriphenylphosphine palladium (25 mg, 0.0222 mmol) were added at room temperature, and the mixture was stirred under microwave irradiation at 100° C. for 20 minutes. The reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate, and extracted with hexane/ethyl acetate (4/1). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (60 mg (yield 60%)) was obtained as a colorless crystal.

後処理

  1. extractionextracted with hexane/ethyl acetate (4/1)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-f760e33cd0fd41e19a7c9d7b7cdaeb20
出典データセット
uspto-grants-2013_10
特許番号
US08551985B2

反応ノート

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