These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-fluorobenzonitrile, its application will become more common.
Application of 179897-89-3,Some common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.
Example 7: 5-Brorno-N-l,3-thiazol-2-yl-lH-indazol-3-amne SCN[0275] Hydrazine monohydrate (2.6 mL, 52.5 mmol) was added to a solution of 5-bromo- 2-fluorobenzonitrile (3.50 g, 17.5 mmol) in ethanol (50 mL) at room temperature. The mixture was stirred for 4 h under reflux condition. After cooling, the mixture was diluted with EtOAc (300 mL), washed with H2O and brine, dried (MgSO4), filtered, and concentrated in vacuo. Purification by recrystallization (EtOAc-hexane) gave 3.37g (91%) of 5-bromo- lH-indazol-3-amine (compound 7A) as a white solid. 1H NMR (300 MHz, CDCl3) delta 4.07 (brs, 2 H) 7.20 (d, IH77=8.85 Hz) 7.42 (dd, IH, J=8.85, 1.70 Hz) 7.71 (d, IH, 7=1.51 Hz) 8.98 (brs, 1 H). MS (ES) [m+H] calc’d for C7H6BrN^, 213; found 211, 213. [0276] Ammonium thiocyanate (229 mg, 3 mmol) was added to a suspension of 5-bromo- lH-indazol-3-amine (212 mg, 1 mmol) in IN hydrochloric acid (3 mL). The mixture was stirred for 4 days at 1000C. The precipitate was collected, and washed with eta2O to give 231 mg (85%) of N-(5-bromo-lH-indazol-3-yI)thiourea (compound 7B) as a yellow solid. 1H NMR (300 MHz, DMSO-rf6) delta 7.43 (d, IH, 7=8.85 Hz) 7.50 (dd, IH, 7=8.85, 1.88 Hz) 8.49 (d, IH, 7=1.32 Hz) 8.79 (brs, IH) 9.18 (brs, IH) 10.85 (s, IH) 12.86 (s, IH). MS (ES) [m+H] calc’d for C8H7BrN4S, 272; found 270, 272.[0277] To a stirred solution of N-(5-bromo-lH-indazol-3-yl)thiourea (104 mg, 0.38 mmol) in ethanol (2 mL) and H2O (1 mL) was added 1 ,2-dichloroethyl ethyl ether (0.05 mL, 0.41 mmol) at room temperature. The mixture was stirred for 3 h at 8O0C. After dilution with EtOAc, the organic layer was washed with H2O and brine, dried (MgSO4), filtered, and concentrated in vacuo. Crystallization from EtOAc-diisopropyl ether gave 62.7 mg (55%) of 5-Bromo-N-l,3-thiazol-2-yl-lH-indazol-3-amine (compound 7) as a white solid. 1H NMR (300 MHz, DMSO-^6) delta 7.01 (d, IH, 7=3.58 Hz) 7.36 (d, IH, 7=3.58 Hz) 7.37 – 7.42 (m, IH) 7.44 – 7.49 (m, IH) 8.35 (d, IH, 7=1.32 Hz) 11.34 (brs, IH) 12.53 (s, IH). MS (ES) [m+H] calc’d for C10H7BrN4S, 296; found 294, 296.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-fluorobenzonitrile, its application will become more common.
Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA SAN DIEGO, INC.; WO2007/75847; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts