Water → 4-(6-Fluoropyridin-3-yl)benzonitrile

HRID 449331Notes

Reaction equation

HRID 449331 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[F:10][C:11]1[N:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.CO>[F:10][C:11]1[N:16]=[CH:15][C:14]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12162Benzonitrile, 4-bromo-HCID 2783397(6-Fluoropyridin-3-yl)boronic acid

Product 1

HCID 231159914-(6-Fluoropyridin-3-yl)benzonitrileYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-bromobenzonitrile (0.20 g, 1.1 mmol), (6-fluoropyridin-3-yl)boronic acid (0.15 g, 1.1 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloromethane (1:1) complex (0.04 g, 0.05 mmol) and potassium carbonate (0.46 g, 3.3 mmol) in 1,4-dioxane (7 mL), and water (3 mL) was heated at 110° C. for 2 h. After cooled to r.t., the mixture was diluted with MeOH, filtered, concentrated under reduced pressure and purified by flash chromatography on a silica gel column eluting with 5% MeOH in DCM to afford the desired product (0.17 g, yield: 78%). Analytic LCMS (M+H)+: m/z=199.2.

Workup

  1. temperatureAfter cooled to r.t.
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash chromatography on a silica gel column
  5. washeluting with 5% MeOH in DCM

Sources & evidence

ORD record
ord-dedfe38c20a048b2b5132e59a29cbaa0
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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