Electric Literature of 1647-26-3, These common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 29A 2-(Trimethylsilyl)ethyl (1RS,2RS,5SR)-2-[4-(2-cyclohexylethoxy)benzoyl]-5-{[4-oxo-6-(trifluoromethyl)-1,2,3-benzotriazin-3(4H)-yl]methyl}cyclopentanecarboxylate (racemate) To a solution of 293 mg (0.36 mmol, 70% purity) of the compound from Example 14A in 2 ml of DMF under argon were added 49 mg (0.43 mmol) of potassium tert-butoxide. After stirring at RT for 5 min, 83 mg (0.44 mmol) of (2-bromoethyl)cyclohexane were added, and the mixture was stirred at bath temperature 100 C. for 2 h. After cooling to RT, 60 ml of water and 60 ml of ethyl acetate were added to the mixture. After separating the phases, the aqueous phase was extracted once with 30 ml of ethyl acetate. The combined organic phases were washed once with 80 ml of saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was taken up in dichloromethane and purified by column chromatography (25 g of silica gel, eluent: cyclohexane/ethyl acetate 9:1). 124 mg (51% of theory, 100% purity) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=8.52 (s, 1H), 8.45 (s, 2H), 7.93 (d, 2H), 7.03 (d, 2H), 4.64-4.48 (m, 2H), 4.14-3.98 (m, 3H), 3.65-3.45 (m, 2H), 3.22 (t, 1H), 2.97-2.84 (m, 1H), 2.18-2.06 (m, 1H), 2.05-1.94 (m, 1H), 1.83-1.52 (m, 8H), 1.50-1.38 (m, 1H), 1.30-1.08 (m, 4H), 1.02-0.87 (m, 2H), 0.36-0.20 (m, 2H), -0.19 (s, 9H). LC/MS (Method 1, ESIpos): Rt=1.74 min, m/z=672 [M+H]+.
Statistics shows that 1-Bromo-2-cyclohexylethane is playing an increasingly important role. we look forward to future research findings about 1647-26-3.
Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMANN, Andreas; BROHM, Dirk; JOeRISSEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (91 pag.)US2017/22171; (2017); A1;,
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