Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 6955

Reaction equation

HRID 6955 reaction equation
[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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 27376517-Hydroxyindole

Product 1

HCID 150540207-(Cyanomethoxy)indole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-586c518b04a74c998bdaf509414209bb
Source dataset
uspto-grants-2006_08
Patent number
US07084169B2

Linked notes

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