Electric Literature of 1211580-54-9 ,Some common heterocyclic compound, 1211580-54-9, molecular formula is C6H4BrF2N, 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.
To a mixture of 4-bromo-2-(difluoromethyl)pyridine (compound I-3a, 416 mg, 2.0 mmol) and diphenylmethanimine (725 mg, 4.0 mmol) in toluene (15 mL) were added Pd2(dba)3 (92 mg, 0.1 mmol), i-BuXPhos (85 mg, 0.2 mmol) and NaOi-Bu (577 mg, 6 mmol). The reaction mixture was heated at 100 C for 2 hours. The reaction mixture was cooled down, diluted with EtOAc (30 mL), and washed with water. The organic layer was separated and concentrated to give crude compound I-3b (617 mg). MS obsd. (ESI+) [(M+H)+]: 309. Compound I-3b (617 mg, 2 mmol) was dissolved in THF (10 mL) and hydrochloride acid (2 mL, 12 M). The resulting mixture was stirred at room temperature for 2 hours, and then concentrated. The residue was dissolved in DCM (5 mL), followed by addition of DIPEA (1 mL, 5.8 mmol) and phenyl carbonochloridate (251 mu, 2.0 mmol) at 0 C. The resulting mixture was stirred at room temperature for 2 hours, and then poured into water (20 mL), and extracted with EtOAc (20 mL) twice. The organic layers were combined and concentrated, and the residue was purified by column chromatography (eluting with 0 ~20 EtOAc in petroleum ether) to afford intermediate 1-3 (264 mg) as a white solid. MS obsd. (ESI+) [(M+H)+]: 265
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1211580-54-9, its application will become more common.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xingchun; LIN, Xianfeng; SHEN, Hong; HU, Taishan; ZHANG, Zhisen; (96 pag.)WO2018/11163; (2018); A1;,
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