Water → 2,6-Bis(4-(trifluoromethyl)phenyl)-4-pyridinecarbonitrile

HRID 1479835Notes

Reaction equation

HRID 1479835 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4](Cl)[N:3]=1.O.C(=O)(O)[O-].[Na+].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>C(COC)OC>[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([C:22]3[CH:23]=[CH:24][C:19]([C:18]([F:29])([F:28])[F:17])=[CH:20][CH:21]=3)[N:3]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 7359062,6-DichloroisonicotinonitrileHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 6337832,6-Bis(4-(trifluoromethyl)phenyl)-4-pyridinecarbonitrileYield 30%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2-6-dichloropyridine-4-carbonitrile 24 (3.7 g, 21.35 mmol) was dissolved in 100 ml of dimethoxyethane. To the solution were added 70 ml of water, sodium bicarbonate (3 equiv., 5.38 g), [4-(trifluoromethyl)phenyl]boronic acid (2.4 equiv., 9.74 g) and the mixture was stirred at rt for 5′. The mixture was degassed and put under argon. A catalytic amount of tetrakispalladium was added and the mixture was heated at 100° C. overnight. The solvents were evaporated off and the residue was dissolved with ethyl acetate, washed with water and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The crude was crystallized from ethyl acetate and petroleum ether to give 28A as a beige solid. (2.5 g, 30% yield)

Workup

  1. customThe mixture was degassed
  2. additionA catalytic amount of tetrakispalladium was added
  3. temperaturethe mixture was heated at 100° C. overnight
  4. customThe solvents were evaporated off
  5. dissolutionthe residue was dissolved with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe crude was crystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-d3ffdb197f6446a2adfed78cb5839e4f
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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