Potassium Carbonate → 4-Methylene-6-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-2,3-dihydropyrano[3,2-b]pyridine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a stirred mixture of Pd2(dba)3 (270 mg, 0.3 mmol), xantphos (870 mg, 1.5 mmol), K2CO3 (1.52 g, 11 mmol) and 3-(4-methylthiazol-2-yl)pyridine (1.76 g, 10 mmol) in a sealed tube was added 6-bromo-4-methylene-2,3-dihydropyrano[3,2-b]pyridine (2.49 g, 11 mmol) in 1,4-dioxance (30 mL). The mixture was stirred at 120° C. for 18 hours. The mixture was diluted with Ethyl acetate and H2O, the organic layer was washed with brine and water, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography (petroleum/Ethyl acetate=3/1) to give the title compound as red solid (710 mg, 22%). 1H NMR (400 Mz, DMSO-d6): δ: 2.69 (s, 3H); 2.81 (t, J=6, 2H); 4.25 (t, J=5.1, 2H); 5.16 (s, 1H); 6.16 (s, 1H); 7.38 (d, J=8.7, 1H); 7.55-7.50 (m, 1H); 7.6 (d, J=8.7, 1H); 8.31-8.27 (m, 1H); 8.66-8.64 (m, 1H); 9.12 (s, 1H).

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