2,3-Butanediol → 2-(4-Formylphenyl)isonicotinonitrile

HRID 1531810Notes

Reaction equation

HRID 1531810 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[F-].[Cs+].C[CH:13]([OH:17])[CH:14](O)[CH3:15]>C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:13]([C:14]1[CH:15]=[CH:7][C:6]([C:2]2[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=2)=[CH:5][CH:4]=1)=[O:17]

Participants

6

Reactant 3

HCID 2622,3-ButanediolHCID 25953Cesium fluorideHCID 117355442-Bromo-4-cyanopyridine

Product 1

HCID 27638682-(4-Formylphenyl)isonicotinonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

Benzaldehyde-4-boronic acid (1.36 g), 2-bromo-4-cyano pyridine (1.5 g), cesium fluoride (2.72 g) and tetrakis(triphenylphosphine)palladium(0) (285 mg) were mixed together in dimethyl ethylene glycol (30 ml ). The reaction mixture was refluxed for 16 hrs under a atmosphere of nitrogen after which time the cooled mixture was diluted with diethyl ether (40 ml ) and washed with water (40 ml), the organic layer was separated and washed with saturated brine, dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography eluting with Dichloromethane/Diethyl ether (97.5/2.5, v/v) to afford the title compound (0.81 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hrs under a atmosphere of nitrogen after which time the cooled mixture
  2. washwashed with water (40 ml)
  3. customthe organic layer was separated
  4. washwashed with saturated brine
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography
  8. washeluting with Dichloromethane/Diethyl ether (97.5/2.5

Sources & evidence

ORD record
ord-4eaf23ffa284444e9eccd9d9668b9518
Source dataset
uspto-grants-2001_03
Patent number
US06200978B1

Reaction notes

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