Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, A new synthetic method of this compound is introduced below., 33863-76-2
To a mixture of 8-(l-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6- carboxamide (350 mg, 1.01 mmol, single enantiomer, [a]D2o: +35 in acetonitrile), cesium carbonate (1288 mg, 3.95 mmol), (9,9-dimethyl-9H-xanthene-4,5- diyl)bis(diphenylphosphine) (147 mg, 0.25 mmol) and l-bromo-3-chloro-5-fluorobenzene (467 mg, 2.23 mmol) in degassed 1,4-dioxane (2ml), was addedtris(dibenzylideneacetone)dipalladium (70 mg, 0.08 mmol). The suspension was heated in a sealed container at 95C for 16 hrs. The reaction mixture was filtered through a short pad of dicalite and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with 0 to 8% isopropanol in DCM. The solvent was evaporated to dryness, the product triturated with diethyl ether – DCM (9: 1), collected by filtration and dried to afford 8-(l-(3-chloro-5-fluorophenylamino)ethyl)-N,N- dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (320 mg; 67%) as a clear yellow solid. Mass Spectrum: M+H+ 474. [a]D20: -138. NMR Spectrum (DMSOd6): 1.52 (d, 3H), 2.75 (bs, 3H), 2.95 (bs, 3H), 3.49-3.63 (m, 4H), 3.70-3.79 (m, 4H), 4.98-5.07 (m, 1H), 5.60 (s, 1H), 6.23 (d, 1H), 6.42 (d, 1H), 6.43 (ddd, 1H), 6.94 (d, 1H), 7.54 (d, 1H), 7.80 (d, 1H).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARLAAM, Bernard, Christophe; DEGORCE, Sebastien, Louis; LAMBERT-VAN DER BREMPT, Christine, Marie, Paul; MORGENTIN, Remy, Robert; PLE, Patrick; WO2011/51704; (2011); A1;,
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