Reference of 50638-47-6, A common heterocyclic compound, 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, molecular formula is C7H6BrClO, 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 13i 5-(3-Bromophenyl)-5-(3-chloro-4-methoxyphenyl)-5H-pyrrolo[3,4-b]pyridin-7-amine n-Butyllithium (0.750 mL, 1.20 mmol) was added to a solution of 4-bromo-2-chloro-1-methoxybenzene (244 mg, 1.10 mmol) in THF (1.5 mL) at -78 C. under an argon atmosphere. The mixture was stirred for 5 min, then a solution of N-((3-bromophenyl)(2-cyanopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide (390 mg, 1 mmol) in THF (1.5 mL) was added. The resulting mixture was stirred at -78 C. for 15 min, then the cooling bath was removed and the mixture was stirred at rt for 1.5 h. Hydrogen chloride in methanol (3 mL, 3.75 mmol) was added and the mixture was stirred at rt for 1 h. Saturated aqueous NaHCO3 (3 mL) was added followed by DCM (3 mL). The mixture was poured into a phase separator and the organic phase was collected, concentrated and purified on a silica gel column eluted with 0-5% 0.1M NH3 in MeOH in DCM to afford 355 mg (83% yield) of the title compound: 1H NMR (500 MHz, DMSO-d6) delta ppm 8.65 (d, 1H) 8.33 (dd, 1H) 7.49 (dd, 1H) 7.41-7.47 (m, 2H) 7.29-7.36 (m, 2H) 7.22-7.29 (m, 2H) 7.06 (d, 1H) 6.90 (br. s., 2H) 3.81 (s, 3H); MS (ES+) m/z 428, 430 [M+1]+.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; ASTRAZENECA AB; US2010/125081; (2010); A1;,
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