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

HRID 1712080Notes

Reaction equation

HRID 1712080 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].[F:17][C:18]1[CH:19]=[C:20]([Mg]Br)[CH:21]=[CH:22][C:23]=1[F:24]>C1COCC1>[F: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[F:24]

Participants

4

Reactant 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178505835HCID 178505835, compound

Product 1

HCID 592052103-{3-[(3,4-Difluoro-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-difluorophenylmagnesium 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 dichloromethane to yield 3-{3-[(3,4-difluoro-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 dichloromethane

Sources & evidence

ORD record
ord-d6384a92aae64197a12e3ce16757d7ee
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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