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

HRID 2242131Notes

Reaction equation

HRID 2242131 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[O:24][CH3:25]>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[O:24][CH3:25]

Participants

4

Reactant 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178491915HCID 178491915, compound

Product 1

HCID 592051783-{3-[(3-Fluoro-4-methoxy-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 (15 mg, 0.075 mmol) in THF (1 mL) at −78° C. was added 0.5 M 3-fluoro-4-methoxyphenylmagnesium bromide in THF (0.3 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-fluoro-4-methoxy-phenyl)-hydroxy-methyl]-pyridin-4-yl}-benzonitrile as a colorless oil.

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-21d2ee70bffd48cf81e453570936b556
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

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