Sodium Carbonate → 2-Chloro-6-(4-ethylphenyl)-3-(trifluoromethyl)pyridine

HRID 603476Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:25]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)[CH3:26]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4]([C:30]2[CH:31]=[CH:32][C:27]([CH2:25][CH3:26])=[CH:28][CH:29]=2)[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2,6-dichloro-3-trifluoromethylpyridine (1 g, 4.54 mmol) in a mixture of toluene (11 mL), 1,4-dioxane (5.88 mL), and water (5.88 mL) were added sodium carbonate (0.96 g, 9.07 mmol), 4-ethylphenyl boronic acid (0.61 g, 4.08 mmol), and PdCl2(dppf)CH2Cl2 (0.75 g, 0.92 mmol). The mixture was stirred at 80° C. for 4 h, and then concentrated under reduced pressure. The product (0.69 g, 53%) was isolated after silica gel flash chromatography (2:1 hexanes/EtOAc). 1H NMR (400 MHz, CD3OD) δ 8.15 (d, 1H), 8.01 (d, 2H), 7.95 (d, 1H), 7.33 (d, 2H), 2.71 (q, 2H), 1.27 (t, 3H).

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8bf2ce335c794a999a69b0dea607a680
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906653B2

Reaction notes

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