7-Bromoindole → 1H-Indole-7-carbonitrile

HRID 1666796Notes

Reaction equation

HRID 1666796 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[Cu](C#N)[C:12]#[N:13]>O.C(OCC)(=O)C>[C:12]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2)#[N:13]

Participants

4

Reactant 2

HCID 27570207-BromoindoleHCID 178418260HCID 178418260, compound

Product 1

HCID 108988161H-Indole-7-carbonitrileYield 54.8%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
200 °C

Procedure

Combine 7-bromoindole (4.72 g, 24.0 mmol) and copper cyanide (4.30 g, 48.1 mmol) in 1-methyl-2-pyrrolidine (40 mL). Heat to 200° C. After 2.5 hours, cool to room temperature, add water-ethyl acetate (200 mL, 1/1) to give a solid. Filter through the celite, extract the filtrate with ethyl acetate, combine the organic layers, wash with brine, dry over Na2SO4, filter and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with hexanes:ethyl acetate (10:1) to give (1.87 g) of the title compound as a yellow solid: 1H NMR (300 MHz, DMSO-d6)) 6.64-6.66 (m, 1H), 7.17 (t, 1H, J=7.6 Hz), 7.51-7.53 (m, 1H), 7.60-7.62 (m, 1H), 7.94 (d, 1H, J=8.0H), 12.03 (br, 1H).

Workup

  1. temperaturecool to room temperature
  2. customto give a solid
  3. filtrationFilter through the celite
  4. extractionextract the filtrate with ethyl acetate
  5. washwash with brine
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue

Sources & evidence

ORD record
ord-3eaf0ef7b27f434996970d12e4626f32
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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