反应详情

A mixture of 4-bromo-2,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-one (0.11 g, 0.34 mmol), 5-methyl-2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenoxy)methyl)pyridine (0.1 g, 0.37 mmol), and Cs2CO3 (0.55 g, 1.86 mmol) in toluene (7 mL) and water (3 mL) was degassed, Pd(dppf)Cl2 (0.058 g, 0.07 mmol) was added under an inert atmosphere and the mixture was degassed again. Then the reaction was refluxed for 2 h and was filtered through a pad of Celite®. The filtrate was diluted with EtOAc (50 mL), washed with water (20 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 2,2-dimethyl-4-(4-((5-methylpyridin-2-yl) methoxy)phenyl)-5-(pyridin-4-yl)furan-3(2H)-one (70 mg, 48%) as a solid. 1H NMR (500 MHz, d6-DMSO): δ 8.72 (d, J=8.5 Hz, 2H), 8.42 (t, J=7.9 Hz, 1H), 7.70 (d, J=8.2 Hz, 2H), 7.63 (t, J=8.2 Hz, 1H), 7.52-7.43 (m, 3H), 7.18 (d, J=7.4 Hz, 2H), 7.11 (d, J=7.5 Hz, 2H), 5.18 (s, 2H), 2.35 (s, 3H), 1.54 (s, 6H). MS: [M+H]: m/z=387.0. HPLC: 91.4% (RT-1.73 min), Column: Acquity BEH-C-18, 50×2.1 mm, 1.7 um. Mobile Phase: 0.025% TFA in Water (A), ACN (B), Flow rate: 0.5 ml/min (Gradient).

1. customwas degassed
2. customthe mixture was degassed again
3. temperatureThen the reaction was refluxed for 2 h
4. filtrationwas filtered through a pad of Celite®
5. additionThe filtrate was diluted with EtOAc (50 mL)
6. washwashed with water (20 mL), brine (20 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto obtain the crude product
11. customThe crude material was purified via silica gel column chromatography