The origin of a common compound about 654-70-6

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General procedure: Thionyl chloride (4.3 g, 36 mmol) was added dropwise under argon to a solution of bromoacid 39 (5.5 g, 30 mmol) in 35 mL of DMA at -5 to -10 C. The resulting mixture was stirred for 2 h under the same conditions. A solution of the appropriate aniline (30 mmol) in 40 mL of DMA was added dropwise to the above solution, and the resulting mixture was stirred overnight at room temperature. The solvent was removed on rotavapor using high vacuum oil pump; the residue was diluted with saturated NaHCO3 solution, and extracted with ethyl ether (3 x 100 mL). Combined extracts were dried over anhydrous Na2SO4, filtered through celite, and purified by flash chromatography on silica gel, using DCM as eluent to afford the desired product. The data are in accordance with literature data [ref]. 1H-NMR (CDCl3): 9.09 (s,1H), 8.12 (d, J = 2.0 Hz, 1H), 7.98 (dd, J = 8.5 Hz, 2.0 Hz, 1H), 7.83 (d, J = 8.5 Hz,1H), 4.02 (d, J = 10.6 Hz, 1H), 3.62 (d, J = 10.6 Hz, 1H), 1.66 (s, 3H); 19F-NMR(CDCl3): -63.59 (s, 3F).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Cyano-3-trifluoromethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bassetto, Marcella; Ferla, Salvatore; Pertusati, Fabrizio; Kandil, Sahar; Westwell, Andrew D.; Brancale, Andrea; McGuigan, Christopher; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 230 – 243;,
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