Some common heterocyclic compound, 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, molecular formula is C12H13BrO2, 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. name: Methyl 1-(4-bromophenyl)cyclobutanecarboxylate
Step 1. Methyl l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)cyclobutane-l -carboxylate: Into a 40 ml vial equipped with a magnetic stir bar and under N2 were added 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2- dioxaborolane (2.26 g, 8.92 mmol), methyl l-(4-bromophenyl)cyclobutanecarboxylate (2 g, 7.43 mmol), Pd(dppf)C12, complex with DCM (307.18 mg, 371.56 muiotatauiotaomicron) and potassium acetate (2.19 g, 22.29 mmol). The vial was evacuated under vacuum and refilled with N2. DMF (15 mL) was added, and the mixture was degassed for 10 minutes with N2 and then heated to 100 C O/N. The black reaction mixture was cooled to RT, and purified by column chromatography through silica gel eluting with 100:0 to 0: 100 Hexanes:EtOAc as a gradient over 25 minutes. The desired fractions were combined, concentrated and further dried under high vacuum O/N to provide a yellow solid (1.6 g) LCMS (ESI+) m/z = 317 (M+l).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1236357-65-5, its application will become more common.
Reference:
Patent; TEMPEST THERAPEUTICS, INC.; POWELL, David Andrew; ROPPE, Jeffrey Roger; SEIDERS, Thomas Jon; DING, Jinyue; SHENG, Tao; JACINTHO, Jason Duarte; (65 pag.)WO2019/79614; (2019); A1;,
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