Related Products of 749927-69-3, These common heterocyclic compound, 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, 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 stirred suspension of zinc powder (2.5 g, 38.5 mmol) in anhydrous N,N-d m ethyl form a ide (10 mL) under nitrogen was added iodine (200 mg). After 5 min, a solution of methyl (f?)-2-((/er/-butoxycarbonyl)amino)-3-iodopropanoate (5.0 g, 15.2 mmol) in A( A’-di m ethyl form a i de (10 mL) was added slowly over lOmin. The mixture was stirred at rt for 30min. A suspension of 4-bromo-2-fluoro-Af- methylbenzamide (2.8 g, 12 mmol), Pd2(dba)3 (280 mg, 0.3 mmol), and 2- dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (Sphos, 250 mg, 0.6 mmol) in /V,/V- dimethylformamide (10 mL) was added into the zinc reagent mixture. The reaction mixture was heated at 50C and stirred overnight. After cooling, the reaction mixture was quenched with water, diluted with EtOAc and filtered through Celite. The filter cake was washed with EtOAc and the filtrate was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography over silica gel (0-80% EtO Ac/hexane) to afford the desired product as a beige solid (4.0 g, 94%). LC-MS: 377.1 [M+Na]+; 1H NMR (400MHz, CDCl3) d 8.04 (t, 1H, J = 8.1 Hz), 7.02 (d, 1H, J = 8.0 Hz), 6.91 (d, 1H, J = 12.8 Hz), 6.70 (m, 1H), 5.02 (d, 1H, J = 8.0 Hz), 4.60 (m, 1H), 3.73 (s, 3H), 3.18 (dd, 1H, J = 13.8, 5.4 Hz), 3.07 (m, 1H), 3.03 (d, 3H, J = 4.6 Hz), 1.43 (s, 9H).
The synthetic route of 749927-69-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; EPIODYNE, INC.; MEDINA, Julio Cesar; MCGEE, Larry; WEI, Zhi-Liang; SADLOWSKI, Corinne; SEIDL, Frederick; BHATT, Ulhas; WANG, Xiaodong; NGUYEN, Thomas; SPERANDIO, David; DING, Pingyu; NERURKAR, Alok; LI, Yihong; DUQUETTE, Jason; (307 pag.)WO2019/195634; (2019); A1;,
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