Chemical compounds
A compound, selected technology, applied in the direction of drug combination, organic chemistry, anhydride/acid/halide active ingredients, etc.
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Embodiment 1
[0291] Example 1 ( 3 ): (2E)-3-{4-[1-ethyl-2,2-bis(4-hydroxyphenyl)vinyl]phenyl}-2-acrylic acid ( 3 )
[0292]
[0293] Step 1: 4,4'-[2-(4-Bromophenyl)-1-butene-1,1-diyl]diphenol (1)
[0294] TiCl under nitrogen atmosphere 4 (9.3 mL, 86 mmol) was added slowly (dropwise) to a stirred suspension of room temperature zinc powder (11.2 g, 172 mmol) in THF (200 mL). The resulting reaction mixture was heated to reflux for 1 hour. A mixture of bis(4-hydroxyphenyl)methanone (3.69 g, 17.2 mmol) and 1-(4-bromophenyl)-1-propanone (11.0 g, 51.62 mmol) in THF (100 mL) was then added, followed by Reflux for another 2 hours. Standard work-up for McMurry coupling reactions followed. The term "standard workup" as used herein generally refers to the standard workup of the McMurry reaction as follows: the reaction mixture was allowed to cool to room temperature and slowly poured into 10% aqueous K 2 CO 3 (500mL). The reaction mixture was filtered through Celite and the solid was washe...
Embodiment 2
[0303] Example 2 ( 7 ): (2E)-3-{4-[1-ethyl-2,2-bis(4-hydroxyphenyl)vinyl]phenyl}-2-acrylamide ( 7 )
[0304]
[0305] Step 1: (2E)-3-(4-{2,2-Bis(acetyloxy)phenyl]-1-ethylvinyl}phenyl)-2-propenoic acid 1,1-dimethylethyl ester( 4 )
[0306] To (2E)-3-{4-[1-ethyl-2,2-bis(4-hydroxyphenyl)vinyl]phenyl}-2-propenoic acid 1,1-dimethylethyl ester 2 (0.500g, 1.13mmol) in CH 2 Cl 2 (75 mL) was slowly added to a stirred solution of Et 3 N (2 mL), DMAP (12 mg) and acetic anhydride (2 mL). The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with CH 2 Cl 2 (150 mL), washed with water and brine, then dried (Na 2 SO 4 ),filter. The filtrate was concentrated, and the crude product was passed through SiO 2 Purification by column chromatography afforded 0.465 g (78%) of the title product 4 , and this product was used in the next step without further purification.
[0307] Step 2: (2E)-3-(4-{2,2-bis[4-(acetyloxy)phenyl]-1-ethylvinyl}...
Embodiment 3
[0316] Embodiment 3 ( 8 ): 4,4'-{2-[4-(3,5-dimethyl-4-isoxazolyl)phenyl]-1-butene-1,1-diyl}diphenol ( 8 )
[0317]
[0318]4,4'-{2-[4-(3,5-dimethyl-4-isoxazolyl)phenyl]-1-butene-1,1-diyl}diphenol ( 8 )
[0319] Under nitrogen atmosphere, add 4,4′-[2-(4-bromophenyl)-1-butene-1,1-diyl]diphenol to the round bottom flask 1 (0.200g, 0.51mmol), PdCl 2 (PPh 3 ) 2 (0.035g, 0.051mmol), 3,5-dimethyl-4-isoxazolyl) boronic acid (0.141g, 1.0mmol), Na 2 CO 3 (0.107 g, 1.0 mmol), THF (4 mL) and water (1 mL). The reaction mixture was refluxed for 3 hours, then cooled to room temperature, diluted with EtOAc (100 ml), washed with H 2 O and brine washed, dried (Na 2 SO 4 ), and concentrated under reduced pressure. The crude product was passed over SiO with hexane:EtOAc (19:1 to 1:1) 2 Purification by chromatography afforded 0.19 g (91%) of the title compound 8 , as an off-white solid.
[0320] 1 H NMR (400MHz, DMSO-d 6 ): δ 0.87(t, J=7.2Hz, 3H), 2.16(s, 3H), 2.34(s, 3H), 2.44...
PUM
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