Some common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, 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. Computed Properties of C13H18N2O2
To a solution of 2-bromo-3-((4-fluorophenyl)ethynyl)pyridine (intermediate 42, 340 mg, 1.23inmol) in anhydrous toluene (15 rnL) was added Pd2(dba)3 (113 mg, 0.123 mmol), XPhos (117 rng,0.246 mmoi) and potassium tert-butoxide (414 mg, 3.69 mrnol) under N2. After 10 mm, tert-butyl5-aminoindoline- I -carboxylate (Intermediate 12, 519 mg, 1.75 mmol) was added and the mixturewas stirred at 20 C for 10 mm, Then, the mixture was heated at 100 C for 3hr, EtOAc and waterwere added. The organic phase was separated and dried (Mg504), filtered and concentrated.Purification IFCC. Si02 0:100 to 30:70, EtOAc/heptane) afforded the title compound (330 mg,62%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 129487-92-9, its application will become more common.
Reference:
Patent; JANSSEN PHARMACEUTICA NV; BERRY, Cynthia G.B.; CHEN, Gang; JOURDAN, Fabrice Loic; LEBOLD, Terry Patrick; LIN, David Wei; PENA PINON, Miguel Angel; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; WU, Dongpei; ZHANG, Wei; AMERIKS, Michael K.; (407 pag.)WO2016/176460; (2016); A1;,
Indoline – Wikipedia,
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