1,4-Dioxane → 3-(3-Formyl-pyridin-4-yl)-benzonitrile

HRID 1712073Notes

Reaction equation

HRID 1712073 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[O:9].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:23][CH2:22]OCC1>C(OCC)(=O)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:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[C:7]1[CH:2]=[C:3]([CH:8]=[CH:22][CH:23]=1)[C:4]#[N:5])=[O:9]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 111167404-Bromopyridine-3-carbaldehyde

Product 1

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A flask was charged with 4-bromo-pyridine-3-carbaldehyde (186 mg, 1 mmol), 3-cyanophenelboronic acid (176 mg, 1.2 mmol), tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol), potassium phosphate (319 mg, 1.5 mmol) and 1,4-dioxane (10 mL). The reaction mixture was kept at 50° C. overnight. The reaction mixture was then diluted with ethyl acetate and washed with water, then brine. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography to yield 3-(3-formyl-pyridin-4-yl)-benzonitrile as white crystals.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-f8ad200adafb4c29afc66f1a6e9a1c03
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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