Adding a certain compound to certain chemical reactions, such as: 109240-30-4, 1-(4-Bromophenyl)cyclopropanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 109240-30-4, blongs to alcohols-buliding-blocks compound. Formula: C9H9BrO
A 5-mL vial was charged with N,N-bis(4-methoxybenzyl)-5-(((3S)-3-(l- propyn-l-yl)-l-piperazinyl)sulfonyl)-2-pyridinamine (0.128 g, 0.246 mmol, Intermediate C), RuPhos palladacycle/RuPhos (1 : 1) (0.033 g, 0.028 mmol, Strem Chemical Inc., Newburyport, MA), l-(4-bromophenyl)cyclopropanol (0.0903 g, 0.424 mmol, Bioorg. Med. Chem. Lett., 2010, 20, 887), sodium 2-methylpropan- 2-olate (0.0702 g, 0.730 mmol, Strem Chemical Inc., Newburyport, MA) and 1,4- dioxane (2 mL). The mixture was degassed by bubbling Ar through the mixture for 5 min. The vial was sealed and the mixture was heated at 100 C for 55 min. The reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (20 mL). The combined organic phases were washed with saturated aqueous sodium chloride (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated under a vacuum. The crude product was purified by column chromatography (25 g of silica, 0 to 50% EtOAc in hexanes) to afford 0.0139 g of light yellow residue. A 5 mL microwave vial was charged with this residue (0.0139 g, 0.021 mmol), and TFA (0.5 mL). Trifluoromethanesulfonic acid (0.025 mL, 0.28 mmol, Alfa Aesar, Ward Hill, MA) was added and the mixture was stirred at room temperature for 5 min. Solid NaHC03 was added followed by aqueous saturated NaHC03. The aqueous phase was extracted with EtOAc (2 x 3 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated under a vacuum. The crude product was purified by column chromatography (10 g of silica, 30 to 90% EtOAc in hexanes) to afford l-(4- ((2S)-4-((6-amino-3-pyridinyl)sulfonyl)-2-( 1 -propyn- 1 -yl)- 1 – piperazinyl)phenyl)-l-propanone (0.0070 g) as a white solid. 1H NMR (300MHz, CD3OD) delta ppm 8.30 (d, J= 2.3 Hz, 1 H), 7.89 (d, J= 9.1 Hz, 2 H), 7.73 (dd, J= 2.5, 9.1 Hz, 1 H), 7.00 (d, J= 9.1 Hz, 2 H), 6.61 (d, J = 8.9 Hz, 1 H), 4.78 (br. s., 1 H), 3.82 – 3.61 (m, 3 H), 3.24 (br. s., 1 H), 2.95 (q, J = 7.3 Hz, 2 H), 2.73 (dd, J= 3.2, 11.5 Hz, 1 H), 2.57 (dt, J= 3.1, 11.7 Hz, 1 H), 1.75 (d, J= 2.2 Hz, 3 H), 1.15 (t, J= 7.3 Hz, 3 H). m/z (ESI, +ve ion) 413.2 (M+H)+. GK-GKRP IC50 (Binding) = 0.353 muMu.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109240-30-4, its application will become more common.
Reference:
Patent; AMGEN INC.; ASHTON, Kate; FOTSCH, Christopher H.; KUNZ, Roxanne K.; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark H.; SIEGMUND, Aaron C.; ST. JEAN, JR., David J.; TAMAYO, Nuria A.; YANG, Kevin C.; WO2014/35872; (2014); A1;,
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