53312-81-5, name is 5-Amino-2-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 5-Amino-2-fluorobenzonitrile
To ethyl 3 -fluoro- 1 -methyl-4- [[( 1R)- 1 -methylpropyl] sulfamoyl]pyrrole-2-carboxylate(354 mg, 1.156 mmol) and 5-amino-2-fluoro-benzonitrile (201.7mg, 1.483 mmol) in dry THF(20 mL) at 0C, lithium bis(trimethylsilyl)amide in THF (4.62 mL, 4.62 mmol) was added. Themixture was stirred 1 hour at 0C. The reaction mixture was quenched with NH4C1 solution (30mL) and extracted with EtOAc (5OmL), diluted with brine (50 mL) and extracted again with EtOAc (50 mL). The combine organic layers were dried over sodium sulphate, filtered and concentrated. The residue (dissolved in 1 mL DMF) was purified by column chromatography on silica using a gradient from 10 till 100% EtOAc in heptane. The product fractions wereconcentrated and the solid residue was crystallized from 50 mL warm methanol upon addition of water. The white crystals were filtered off and dried in vacuo at 50C overnight, resulting in compound 186 (306 mg)MethodA: Rt: 1.83 minmlz: 395.1 (M-H) Exactmass: 396.11. ?H NMR (400 MHz, DMSO-d6) oe ppm 0.78 (t, J=7.4 Hz, 3 H), 1.01 (d, J=6.6 Hz, 3 H), 1.31 – 1.44 (m, 2 H), 3.06 – 3.20 (m, 1 H), 3.80 (s, 3 H), 7.47 (d, J=4.6 Hz, 1 H), 7.50 – 7.58 (m, 2 H), 7.96(ddd, J=9.2, 4.8, 2.9 Hz, 1 H), 8.17 (dd, J5.7, 2.6 Hz, 1 H), 10.31 (s, 1 H).
The synthetic route of 53312-81-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
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