These common heterocyclic compound, 1257535-06-0, name is 3-Bromo-4-fluorobenzene-1,2-diamine, 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. Computed Properties of C6H6BrFN2
A 500 mL round-bottomed flask charged with 3-bromo-4-fluorobenzene-l,2-diamine (18 g, 88 mmol), DMF (100 mL), ethyl 2-bromopropionate (Sigma Aldrich, 1 1.54 mL, 89 mmol) and NaHC03, powder (7.60 g, 90 mmol) was heated to 90 C with a reflux condenser for 30 min, then at 120 C for 15 h. The reaction was cooled to RT, treated with brine and extracted with EtOAc (2 x 200 mL), washed with brine (3 x) and dried over Na2S04, filtered and concentrated affording crude 8-bromo-7-fluoro-3-methyl-3,4- dihydroquinoxalin-2(lH)-one (21.75 g, 84 mmol, 96 % yield) as an orange-brown viscous oil. The material was used in the subsequent step without further purification: FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-d6) delta ppm 9.67 (s, 1 H) 6.78 – 6.89 (m, 1 H) 6.48 – 6.78 (m, 1 H) 6.07 – 6.35 (m, 1 H) 1.25 (d, J=6.46 Hz, 3 H). 19F NMR (377 MHz, DMSO-d6) delta ppm -120.49 (1 F, s). m/z (ESI, +ve ion) 259.0/261.0 (M+H)+.
The synthetic route of 3-Bromo-4-fluorobenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.
Reference:
Patent; AMGEN INC.; CEE, Victor J.; BROWN, James; CHAVEZ JR., Frank; CHEN, Jian J.; HERBERICH, Bradley J.; HARRINGTON, Essa Hu; LANMAN, Brian Alan; LEE, Matthew; PETTUS, Liping H.; REED, Anthony B.; TASKER, Andrew; WANG, Hui-Ling; WU, Bin; WURZ, Ryan; WO2014/22752; (2014); A1;,
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