Cesium carbonate → 4-[4-(Trifluoromethyl)phenyl]pyridine-2-carbonitrile

HRID 1479886Notes

Reaction equation

HRID 1479886 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 6933424-Chloro-2-pyridinecarbonitrileHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 841644164-[4-(Trifluoromethyl)phenyl]pyridine-2-carbonitrileYield 89%

Reagents, catalysts & solvents 2

HCID 86647063palladium(II) acetate 2-(dicyclohexylphosphino)-2',4',6'-triisopropyl-1,1'-biphenylCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4-Chloropyridine-2-carbonitrile 19B (2.0 gr, 14.44 mmol) was dissolved in 35 ml of dioxane. The solution was added with cesium carbonate (6.8 gr), [4-(trifluoromethyl)phenyl]boronic acid (1.2 equiv., 3.3 gr) and palladium acetate/XPhos (80 mg/280 mg) under argon atmosphere. The mixture was stirred at 100° C. for 4 hours. The reaction is filtered through a pad of celite, concentrated and crystallized from diethyl ether/petroleum ether to give a beige solid (3.2 gr, 12.85 mmol, yield: 89%) 1HNMR (DMSO, 400 MHz) δ 7.92 (2H, dd, J=8.0 Hz), 8.12 (3H, m), 8.51 (1H, dd), 8.39 (1H, dd, J=5.2 Hz)

Workup

  1. filtrationThe reaction is filtered through a pad of celite
  2. concentrationconcentrated
  3. customcrystallized from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-16f4211d2c594e6bba416cd467ed538b
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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