Electric Literature of 77326-36-4, These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, 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 solution of 2-ethoxy-N-(trans-4-hydroxycyclohexyl)acetamide (20.10 g, 99.87 mmol) in anhydrous 1,4-dioxane (800 mL), was added portion-wise sodium hydride (4.33 g, 108.25 mmol, 60% in mineral oil) at room temperature under nitrogen. The mixture was stirred for 1 h at room temperature, and then a solution of 2-amino-6-fluorobenzonitrile (11.34 g, 83.30 mmol) in anhydrous 1,4-dioxane (200 mL) was added drop-wise. The reaction mixture was heated at 90 oC over 72 h, cooled to room temperature, concentrated under reduced pressure, ice water (150 mL) was carefully added and extracted with EtOAc (5 x 200 mL). The combined extract was washed with brine, dried over MgSO4, filtered and the solvent was evaporated. The residue was purified by silica gel column chromatography (35% to 65% EtOAc in hexanes) to afford 18.98 g (72%) of the title compound as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 7.18 (t, J = 8.2 Hz, 1H), 6.44 (d, J = 8.2 Hz, 1H), 6.29 (d, J = 8.3 Hz, 1H), 6.21 (d, J = 8.3 Hz, 1H), 4.39 (br s, 2H), 4.31-4.21 (m, 1H), 4.91 (s, 2H), 3.97-3.84 (m, 1H), 3.57 (q, J = 7.0 Hz, 2H), 2.19-2.05 (m, 4H), 1.78-1.63 (m, 2H), 1.44-1.29 (m, 2H), 1.24 (t, J = 7.0 Hz, 3H). MS 318 (MH+).
The synthetic route of 77326-36-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SENOMYX, INC.; PETROVIC, Goran; FOTSING, Joseph; SERVANT, Guy; TACHDJIAN, Catherine; KARANEWSKY, Donald; VONG, Binh; BOREN, Brant, Clayton; CHEN, Qing; ZHANG, Hong; CHING, Brett, Weylan; LAPERA, Stephanie; (99 pag.)WO2016/73251; (2016); A1;,
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