Chemical compounds
A compound, selected technology, applied in the preparation of organic compounds, drug combinations, organic chemistry, etc.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0317] Example 1 ( 3 ): (2E)-3-{3-[1-ethyl-2,2-bis(4-hydroxyphenyl)vinyl]phenyl}-2-acrylic acid ( 3 )
[0318]
[0319] Step 1: 4,4'-[2-(3-Bromophenyl)-1-butene-1,1-diyl]diphenol (1)
[0320] General procedure for McMurry coupling
[0321] Under a nitrogen atmosphere, TiCl was passed through a funnel at room temperature 4 • 2 THF complex (35.0 g, 0.105 mol) was slowly added to a stirred suspension of zinc powder (13.7 g, 0.211 mol) in THF (300 mL). The reaction mixture was heated to reflux for 1.0 hour. A solution of bis(4-hydroxyphenyl)methanone (4.5 g, 0.021 mol) and 1-(3-bromophenyl)-1-propanone (13.42 g, 0.063 mol) in THF (200 mL) was added to the reaction mixture . Under a nitrogen atmosphere, the reaction mixture was heated to reflux with stirring for an additional 2 hours. The reaction mixture was allowed to cool to room temperature. Standard work-up for McMurry coupling reactions followed. The term "standard work-up" as used herein generally refers to the s...
Embodiment 2
[0329] Example 2 ( 6 ): (2E)-3-{5-[1-ethyl-2,2-bis(4-hydroxyphenyl)vinyl]-2-fluorophenyl}-2-acrylic acid ( 6 )
[0330]
[0331] Step 1: 4,4'-[2-(3-bromo-4-fluorophenyl)-1-butene-1,1-diyl]diphenol ( 4 )
[0332] Using bis(4-hydroxyphenyl)methanone (3.60g, 0.0168mol) and 1-(3-bromo-4-fluorophenyl)-1-propanone (11.65g, 0.0504mol) 1 General McMurry steps as described. Purification after standard workup afforded 6.420 g (93%) of the title compound 4 , as an off-white solid.
[0333] 1 H NMR (400MHz, DMSO-d 6 ): δ0.83(t, J=7.2Hz, 3H), 2.38(q, J=7.6Hz, 2H), 6.44(d, J=8.4Hz, 2H), 6.59(d, J=8.4Hz, 2H ), 6.72(d, J=8.4Hz, 2H), 6.95(d, J=8.8Hz, 2H), 7.09-7.05(m, 1H), 7.15(app.t, J=8.8Hz, 1H), 7.36 and 7.34 (dd, J 1 =7.2Hz,J 2 =2.4Hz, 1H), 9.38(s, 1H), 9.41(s, 1H). LCMS (APCI): m / z 413 (M-H) - .
[0334] Step 2: (2E)-3-{5-[1-Ethyl-2,2-bis(4-hydroxyphenyl)vinyl]-2-fluorophenyl}-2-propenoic acid 1,1-dimethyl Ethyl ester ( 5 )
[0335] Under a nitrogen atmosphere, put 4,4′...
Embodiment 3
[0340] Embodiment 3 ( 7 ): 4,4'-{2-[3-(3,5-dimethyl-4-isoxazolyl)phenyl]-1-butene-1,1-diyl}diphenol ( 7 )
[0341]
[0342] 4,4'-{2-[3-(3,5-dimethyl-4-isoxazolyl)phenyl]-1-butene-1,1-diyl}diphenol ( 7 )
[0343] Under nitrogen atmosphere, add 4,4′-[2-(3-bromophenyl)-1-butene-1,1-diyl]diphenol to the round bottom flask 1 (0.200g, 0.51mmol), PdCl 2 (PPh 3 ) 2 (0.024g, 0.034mmol), 3,5-dimethyl-4-isoxazolyl)boronic acid (0.090g, 0.64mmol), aqueous 2MNa 2 CO 3 (0.106 g, 0.5 mL, 1.0 mmol), THF (4 mL) and water (1 mL). The reaction mixture was refluxed for 12 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc (100 ml), washed with H 2 O, washed with brine, dried, and concentrated under reduced pressure to give crude product. The product was passed through SiO using hexane:EtOAc (19:1 to 1:1) as eluent 2 Purification by chromatography afforded 0.100 g (48%) of the title compound 7 , as a white solid.
[0344] 1 H NMR (400MHz, DMSO-d 6 ): ...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More