Extracurricular laboratory: Synthetic route of 2-Fluoropyridine-5-carbaldehyde

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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 677728-92-6, name is 2-Fluoropyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Fluoropyridine-5-carbaldehyde

2) Preparation of (Z)-3-(6-fluoropyridin-3-yl)-2-(5-methoxy-1H-indol-3-yl)-acrylonitrile To a solution of tert-butyl 3-(cyanomethyl)-5-methoxy-1H-indol-1-carboxylate (719 mg, 2.51 mmol, 1.0 eq.) in anhydrous THF (30 mL) was added, under an argon atmosphere, NaH (106 mg, 80%, 3.52 mmol, 1.4 eq.). The mixture was stirred at room temperature for 2 hours, and then cooled to 0 C. before the addition of 6-fluoro-pyridine-3-carbaldehyde (440 mg, 3.52 mmol, 1.4 eq.) in anhydrous THF (6 mL). The reaction apparatus was protected from light and the mixture was stirred at 0 C. for 4 hours, and then quenched with a saturated aqueous ammonium chloride solution. The mixture was stirred again at room temperature for 4 hours and extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. The solvent was removed under reduced pressure, and the residue purified by silica gel flash-column chromatography (eluent: CH2Cl2/EtOH, 98:2) to afford, after trituration with diethyl ether, the compound (28) as a yellow powder (45 mg, 6%). IR numax (cm-1): 2215 (nuCN); 1H NMR (DMSO, 300 MHz): delta (ppm): 3.84 (3H, s, 5′-methoxy), 6.91 (1H, dd, J6′-7’=8.9 Hz, J6′-4’=2.1 Hz, H6′), 7.36 (1H, dd, J5″-4″=8.5 Hz, J5″-F=2.1 Hz, H5″), 7.41 (1H, d, J7′-6’=8.9 Hz, H7′), 7.49 (1H, d, J4′-6’=2.4 Hz, H4′), 7.76 (1H, s, H3), 7.78 (1H, s, H2′), 8.52 (1H, td, J5″-4″=J5″-F=10.1 Hz, J4″-2″=1.8 Hz, H4″), 8.67 (1H, d, J2″-4″=1.8 Hz, H2″), 11.66 (1H, s, indolic H); 13C NMR (DMSO, 75.5 MHz): delta (ppm): 55.6 (5′-methoxy), 102.0 (C4′), 108.2 (C2), 109.7 (1C, d, 2JC-F=37 Hz, C5″), 110.0 (C3′), 112.4 (C6′), 113.2 (C7′), 118.0 (C1), 124.0 (C3a’), 127.7 (C2′), 129.5 (1C, d, 4JC-F=4 Hz, C3″), 130.7 (C3), 132.3 (C7a’), 140.7 (1C, d, 3JC-F=8 Hz, C4″), 148.2 (1C, d, 3JC-F=15 Hz, C2″), 154.6 (C5′), 162.6 (1C, d, 1JC-F=237 Hz, C6″); ESI: 294.1 ([M+H]+), 316.1 ([M+Na]+), 348.1 ([M+Na+ MeOH]+); HRESI-MS: m/z 294.1052 (calcd for C17H13N3OF, 294.1043).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 677728-92-6, 2-Fluoropyridine-5-carbaldehyde.

Reference:
Patent; COMMISSARIAT A L’ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; Guillou, Catherine; Kozielski, Frank; Labriere, Christophe; Gueritte, Francoise; Tcherniuk, Sergey; Skoufias, Dimitrios; Thal, Claude; Husson, Henri-Philippe; US9212138; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem