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

HRID 385854

반응식

HRID 385854 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ee2a1c095a0f42a4906e83ae1ecdd90f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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