Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 6955

반응식

HRID 6955 반응식
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]#[N:20]>C(#N)C>[NH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[O:1][CH2:18][C:19]#[N:20])[CH:7]=[CH:8]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 27376517-Hydroxyindole

생성물 1

HCID 150540207-(Cyanomethoxy)indole

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

In a 100 mL roundbottom flask equipped with a magnetic stirrer and rubber septum, 7-hydroxy-1H-indole (1.66 g., 12.48 mmol) was dissolved 50 mL anhydrous acetonitrile. The flask was charged with potassium carbonate (6.88 g., 49.9 mmol) and cooled to 0° C. While stirring, bromoacetonitrile (1.64 g., 13.73 mmol) was added dropwise over two minutes. The reaction mixture was allowed to warm to ambient temperature and stirring was continued for three hours. The solution was washed with water (2×30 mL) and brine (1×30 mL), dried over MgSO4 and concentrated in vacuo. The resulting oily brown residue was purified by flash chromatography (95:5 ethyl acetate:hexanes to 85:15 ethyl acetate:hexanes over minutes) to give (1H-Indol-7-yloxy)-acetonitrile as a crystalline solid (0.244-g.) ms: (M−H)−=171.2.

후처리

  1. customIn a 100 mL roundbottom flask equipped with a magnetic stirrer
  2. temperatureto warm to ambient temperature
  3. stirringstirring
  4. washThe solution was washed with water (2×30 mL) and brine (1×30 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting oily brown residue was purified by flash chromatography (95:5 ethyl acetate:hexanes to 85:15 ethyl acetate:hexanes over minutes)

출처 및 근거

ORD 기록
ord-586c518b04a74c998bdaf509414209bb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084169B2

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