1,2-Dimethoxyethane → 2-(4-Fluorophenyl)isonicotinonitrile

HRID 1026757Notes

Reaction equation

HRID 1026757 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>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.O.C(O)C>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][N:9]=2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 463120752-(4-Fluorophenyl)isonicotinonitrileYield 73.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-isonicotinonitrile (1.9 g), 4-fluorophenylboronic acid (2.9 g), sodium carbonate (4.3 g), tetrakis(triphenylphosphine)palladium (480 mg), 1,2-dimethoxyethane (40 mL), ethanol (20 mL) and water (20 mL) was stirred while heating at 100° C. for 2 hr. The solvent was distilled off under reduced pressure, and the resulting residue was then purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=94:6-50:50) to afford 2-(4-fluorophenyl)pyridine-4-carbonitrile (2.0 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe resulting residue was then purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=94:6-50:50)

Sources & evidence

ORD record
ord-55b6f545ef874f51a2ef5be5c1514179
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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