Reference of 50397-74-5,Some common heterocyclic compound, 50397-74-5, name is 4-Amino-3-bromobenzonitrile, molecular formula is C7H5BrN2, 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 solution of compound 54-1 (1 g, 5.08 mmol, 1 eq.) in DMF (7 mL) and TEA (2.18 g, 21.55 mmol, 3 mL, 4.25 eq.) was added compound 54-2 (683.15 mg, 6.09 mmol, 783.43 uL, 1.2 eq.),(48.33 mg, 253.77 umol, 0.05 eq.) and Pd(PPh3)2C12 (178.12 mg, 253.77 umol, 0.05 eq.). The mixture was stirred at 90 C under nitrogen atmosphere for 3 hours. TLC showed a new one spot formed. The reaction mixture was diluted with water (20 mL), extracted with EtOAc (20 mLx2),washed with brine (20 mL), dried with sodium sulfate, filtered and concentrated. The residue waspurified by flash silica gel column chromatography (PE:EA = 5:1) to give compound 3 (1 g, yield:86%) as a yellow oil. ?H NMR (400MHz, CDC13) 3 = 7.52 (d, J 1.6 Hz, 1 H), 7.34 (dd, J 8.6, 1.8Hz, 1 H), 6.68 (d, J= 8.4 Hz, 1 H), 4.76 (s, 2 H), 2.95 (s, 1 H), 2.88 (s, 1 H), 2.32 (s, 1 H), 1.85 -1.70 (m,4H), 1.10 (t,J7.4Hz,6H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-3-bromobenzonitrile, its application will become more common.
Reference:
Patent; TREVENA, INC.; PITIS, Philip Michael; BOYD, Robert Eugene; DAUBERT, Tamara Ann Miskowski; HAWKINS, Michael John; LIU, Guodong; SPEERSCHNEIDER, Aimee Crombie; (355 pag.)WO2018/231745; (2018); A1;,
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