Sodium Cyanide → 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile

HRID 562845Notes

Reaction equation

HRID 562845 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C-:11]#[N:12].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:11]([C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)#[N:12]

Participants

7

Reactant 2

HCID 8929Sodium CyanideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 117883551H-Pyrrolo[2,3-b]pyridine-5-carbonitrile

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 5-Bromo-7-azaindole XXX (300 mg, 1.52 mmol) in DMF (10 ml), sodium cyanide (150 mg, 3.06 mmol), cuprous iodide (45 mg, 0.24 mmol), and Tetrakis (triphenylphosphine) palladium(0) (100 mg, 0087 mmol) were added. The reaction was placed under argon heated at 125° C. for 48 hours after which the reaction was allowed to cool to ambient temperature before diluting with ethyl acetate and saturated sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×, 150 ml). The organic layers were then combined and washed with saturated bicarbonate solution (3×, 100 ml), before drying over sodium sulfate and evaporate under reduced pressure. The crude material was purified by preparative TLC, eluting with a solution of 70% hexane, 30% ethyl acetate with triethylamine as an additive to yield the titled compound as an off-white solid. (150 mg, M−1=142.0)

Workup

  1. temperatureto cool to ambient temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×, 150 ml)
  4. washwashed with saturated bicarbonate solution (3×, 100 ml)
  5. dry with materialbefore drying over sodium sulfate
  6. customevaporate under reduced pressure
  7. customThe crude material was purified by preparative TLC
  8. washeluting with a solution of 70% hexane, 30% ethyl acetate with triethylamine as an additive

Sources & evidence

ORD record
ord-cf64fff77b554369b76d42a4e4bb8304
Source dataset
uspto-grants-2011_11
Patent number
US08067434B2

Reaction notes

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