Cesium carbonate → 2,2-dimethyl-5-(pyridin-4-yl)-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one

A mixture of 4-bromo-2,2-dimethyl-5-(pyridin-4-yl)-furan-3(2H)-one (0.25 g, 0.93 mmol), 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl)quinoline (0.37 g, 1.026 mmol), and Cs2CO3 (1.52 g, 4.664 mmol) in 5:1 toluene/water (12 mL) was degassed. Pd(dppf)Cl2 (152.2 mg, 0.18 mmol) was then added under an inert atmosphere and the mixture was again degassed. The reaction mixture was refluxed for 3 h, filtered through a pad of Celite® and the filtrate was diluted with EtOAc (100 mL). The combined organic layers were washed with water (50 mL) and brine (50 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-5-(pyridin-4-yl)-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one (0.29 g, 74%) as a solid. 1H NMR (500 MHz, CDCl3): δ 8.78 (d, J=7.2 Hz, 1H), 8.56-8.50 (m, 2H), 8.15-8.05 (m, 2H), 7.78-7.72 (m, 1H), 7.63-7.59 (m, 1H), 7.56-7.47 (m, 2H); 7.18-7.09 (m, 2H), 7.02-6.96 (m, 3H), 5.40 (s, 2H), 1.50 (s, 6H). MS: M+H: m/z=423.1. LC MS: 98%, Column: Eclipse XDB-C18, 150×4.6 mm, Sum. Mobile Phase: 0.1% TFA in Water (A), AcN (B), Flow rate: 1.5 ml/min (Gradient)

1. customwas degassed
2. customthe mixture was again degassed
3. temperatureThe reaction mixture was refluxed for 3 h
4. filtrationfiltered through a pad of Celite®
5. additionthe filtrate was diluted with EtOAc (100 mL)
6. washThe combined organic layers were washed with water (50 mL) and brine (50 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

ORD 기록

ord-de1aa7ee0ed94ad5bdf1f165c484cec2

출처 데이터셋

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08071595B2