Dimethylformamide → Furo[3,2-C]pyridine-7-carbonitrile

HRID 557183Notes

Reaction equation

HRID 557183 reaction equation
Br[C:2]1[C:3]2[O:10][CH:9]=[CH:8][C:4]=2[CH:5]=[N:6][CH:7]=1.[Cu](C#N)[C:12]#[N:13].CN(C)C=O>C(OCC)C.[Cu](I)I>[O:10]1[C:3]2[C:2]([C:12]#[N:13])=[CH:7][N:6]=[CH:5][C:4]=2[CH:8]=[CH:9]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 179853197-Bromofuro[3,2-c]pyridineHCID 178418260HCID 178418260, compound

Product 1

HCID 17985291Furo[3,2-C]pyridine-7-carbonitrile

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 3283Diethyl EtherSolvent

Procedure

Combine 7-bromofuro[3,2-c]pyridine (4.673 g, 23.5 mmol), copper cyanide (4.21 g, 47.1 mmol), copper iodide (8.96 g, 47.1 mmol), and anhydrous dimethylformamide (100 mL) and at 130° C. for 30 hours. Cool to room temperature, dilute with diethyl ether and wash with 15% aqueous ammonium hydroxide. Extract combined aqueous layers with diethyl ether, wash combined organic layers with 15% aqueous ammonium hydroxide, and brine, dry over magnesium sulfate, and concentrate. Purification using flash chromatography, eluting with hexane:ethyl acetate gives the title compound as a white solid.

Workup

  1. washwash with 15% aqueous ammonium hydroxide
  2. extractionExtract
  3. washwash
  4. dry with materialdry over magnesium sulfate
  5. concentrationconcentrate
  6. customPurification
  7. washeluting with hexane

Sources & evidence

ORD record
ord-70600fdb711a4749a122e604a5d863cb
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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