Potassium Carbonate → HCID 86684921, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2-methylpyridine (6.0 g, 34.9 mmol) was dissolved in dimethylformamide (60 mL) before potassium acetate (10.0 g, 102 mmol) and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (10 g, 39.4 mmol) were added at room temperature. The solution was degassed and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (400 mg, 547 mol) was added. The brown reaction mixture was stirred for 22 h at 80° C. After cooling to room temperature, 3-(4-bromo-2-trifluoromethyl-phenylsulfanyl)-propionamide (8.0 g, 24.4 mmol), potassium carbonate (8.0 g, 57.9 mmol), dimethylformamide (20 mL), and water (16 mL) were added. The mixture was degassed, stirred for 30 min at room temperature and further [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (400 mg, 547·mol) was added. The resulting brown reaction mixture was stirred for 20 h at 60° C. After cooling to room temperature, it was poured onto water (150 mL) and extracted with ethyl acetate (1×80 mL, 2×40 mL). The combined organic extracts were washed with brine/water (1:1 v/v, mL) and brine (20 mL), methanol (16 mL) was added and the mixture was dried over sodium sulfate. Silica gel (16 g) was added, the slurry was filtered and washed with ethyl acetate/methanol (9:1 v/v, 40 mL). The combined filtrates were concentrated in vacuo. The residue was treated with toluene/n-heptane (1:1 v/v, 24 mL) and the resulting suspension was stirred for 30 min at room temperature. After filtration, the precipitate was washed with toluene/n-heptane (4:1 v/v, 10 mL) and n-heptane (10 mL) and dried in vacuo to afford the title compound as brown crystals (5.7 g, 71%). MS (EI): m/z=341.1 [M+H]+. 1H NMR (d6-DMSO, 400 MHz): δ 2.48 (t, J=7.2 Hz, 2H), 2.54 (s, 3H), 3.32 (t, J=7.2 Hz, 2H), 6.95 (bs, 1H), 7.41 (bs, 1H), 7.58 (dd, J=1.6 Hz, 5.4 Hz, 1H), 7.68 (s, 1H), 7.77 (d, J=9.1 Hz, 1H), 8.02-8.08 (m, 2H), 8.52 (d, J=5.1 Hz, 1H).

Provenance & Evidence