Sodium Carbonate → 4-(4-Formylpyridin-3-yl)-2-methylbenzonitrile

HRID 1897570Notes

Reaction equation

HRID 1897570 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Br[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][C:25]=1[CH:26]=[O:27].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:26]([C:25]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([CH3:1])[CH:9]=1)=[O:27]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27629973-Bromopyridine-4-carboxaldehydeHCID 451585202-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 866748334-(4-Formylpyridin-3-yl)-2-methylbenzonitrileYield 78.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1a (430 mg, 1.769 mmol), 3-bromo-4-pyridinecarboxaldehyde (299 mg, 1.608 mmol), sodium carbonate (2N in water, 1.608 mL, 3.22 mmol), bis(triphenylphosphine)palladium(II) chloride (28.2 mg, 0.040 mmol) in DMF (6.432 mL) was heated to 100° C. for 2 hrs. The mixture was quenched with saturated NaHCO3 and extracted with EtOAc two times, dried over magnesium sulfate, filtered and concentrated. The residue was purified via Biotage (0-50% EtOAc/heptane; 25M column) giving compound 1b as white solid (280 mg, 78%). LC-MS (M+1) 223.1, t=1.28 min.

Workup

  1. customThe mixture was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc two times
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via Biotage (0-50% EtOAc/heptane; 25M column)

Sources & evidence

ORD record
ord-6ebd6bad38714eeb8ecf4ce25d5ab0e2
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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