Sodium Cyanide → 2-(6-Bromopyridin-2-yl)acetonitrile

HRID 385854

反応式

HRID 385854 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[N:3]=1.[C-:10]#[N:11].[Na+]>CS(C)=O.C(OCC)(=O)C.O>[Br:1][C:2]1[N:3]=[C:4]([CH2:8][C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 2

HCID 8929Sodium CyanideHCID 129547962-Bromo-6-(bromomethyl)pyridine

生成物 1

HCID 6428642-(6-Bromopyridin-2-yl)acetonitrile

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

A solution of 2-bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (5 g, 19.9 mmol) in dimethylsulfoxide (50 mL) was charged with sodium cyanide (2.93 g, 59.8 mmol). The reaction was heated to 50° C. overnight. Upon completion, the reaction was diluted with ethyl acetate (100 mL) and water (100 mL) and the layers were separated. The organic layer was then dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography (hexane:ethyl acetate 7:3) followed by purification by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier) to afford the title compound.

後処理

  1. customthe layers were separated
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (hexane:ethyl acetate 7:3)
  6. customfollowed by purification by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier)

出典と根拠

ORDレコード
ord-ee2a1c095a0f42a4906e83ae1ecdd90f
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

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