Sodium Carbonate → 4-(5-Formylpyridin-3-yl)benzonitrile

HRID 2407417Notes

Reaction equation

HRID 2407417 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].Br[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH:20]=1)[CH:18]=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:18]([C:17]1[CH:20]=[C:13]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:14]=[N:15][CH:16]=1)=[O:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 595784114-(5-Formylpyridin-3-yl)benzonitrileYield 52.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-cyanophenylboronic acid (735 mg, 5.00 mmol), 5-bromonicotinaldehyde (930 mg, 5.000 mmol), sodium carbonate (5000 μl, 10.00 mmol), bis(triphenylphosphine)palladium(II) chloride (88 mg, 0.125 mmol) in DMF (15 mL, dry) was heated to 120° C. for 3 h. After concentration, the residue was dissolved into CH2Cl2-MeOH, mixed with silica gel and concentrated. Purification by flash column (MeOH—CH2Cl2, v/v, 0%-1%) yielded 4-(5-formylpyridin-3-yl)benzonitrile as colorless solid (550 mg) 1H NMR (400 MHz, CDCl3): δ 7.55 (d, J=8.57 Hz, 2H), 7.82 (d, J=8.57 Hz, 2H), 8.36 (s, 1H), 9.08 (d, J=2 Hz, 1H), 9.12 (d, J=2 Hz, 1H), 10.21 (s, 1H).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved into CH2Cl2-MeOH
  3. additionmixed with silica gel
  4. concentrationconcentrated
  5. customPurification by flash column (MeOH—CH2Cl2, v/v, 0%-1%)

Sources & evidence

ORD record
ord-a68a581abf944e0499594c278391d2fe
Source dataset
uspto-grants-2014_08
Patent number
US08809545B2

Reaction notes

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