3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-{3-[(3,4-Dichloro-phenyl)-hydroxy-methyl]-pyridin-4-yl)-benzonitrile

HRID 2242121Notes

Reaction equation

HRID 2242121 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])=[O:2].[Cl:17][C:18]1[CH:19]=[C:20]([Mg]Br)[CH:21]=[CH:22][C:23]=1[Cl:24]>C1COCC1>[Cl:17][C:18]1[CH:19]=[C:20]([CH:1]([OH:2])[C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:8]=2[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH:21]=[CH:22][C:23]=1[Cl:24]

Participants

4

Reactant 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178478192HCID 178478192, compound

Product 1

HCID 592051853-{3-[(3,4-Dichloro-phenyl)-hydroxy-methyl]-pyridin-4-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(3-formyl-pyridin-4-yl)-benzonitrile (30 mg, 0.15 mmol) in THF (1.5 mL) at −78° C. was added 0.5 M 3,4-dichlorophenylmagnesium bromide in THF (0.6 mL). The reaction mixture was quenched with ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography eluted with 5% methanol in dichlordmethane to yield 3-{3-[(3,4-dichloro-phenyl)-hydroxy-methyl]-pyridin-4-yl}-benzonitrile as white crystals.

Workup

  1. customThe reaction mixture was quenched with ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography
  6. washeluted with 5% methanol in dichlordmethane

Sources & evidence

ORD record
ord-e34534fc393140c08f1d65c7c827dc75
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

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