Some common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, molecular formula is C3H4F3I, 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. Application In Synthesis of 1,1,1-Trifluoro-3-iodopropane
A vial was charged with activated zinc (Rieke Zinc) (4.38 ml, 3.35 mmol) and cooled to 0C. 1,1,1-trifluoro-3-iodopropane (0.268 ml, 2.233 mmol) was added slowly dropwise and the reaction was warmed to room temperature and stirred for one hour. Palladium(II) acetate (2.73 mg, 0.012 mmol), 2?-(dicyclohexylphosphino)-N2,N2,N6,N6- tetramethyl-[ 1,1 ?-biphenylj -2,6-diamine (CPhos) (10.60 mg, 0.024 mmol), and 1 -(4-bromo-5- fluoro-2-methoxyphenyl)-N-(isoxazol-3 -yl)-2-oxo- 1 ,2-dihydroquinoline-6-sulfonamide (See above Intermediate B 1, 0.100 g, 0.202 mmol) were added and the reaction was stirred for two hours at 50 C. The reaction was diluted with ethyl acetate and washed twice with iN HC1 solution. The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 40g, gradient elution 0-100% EtOAc :Heptane) to afford (P)- 1 -(5 -fluoro-2-methoxy-4-(3 ,3,3 – trifluoropropyl)phenyl)-N-(isoxazol-3 -yl)-2-oxo- 1 ,2-dihydroquinoline-6-sulfonamide (0.067 g, 0.131 mmol, 64.8 % yield) as a white solid. 1H NMR (400 MHz, DM50-cl6) oe = 2.64 – 2.78 (m, 2 H) 2.87-3.03 (m, 2 H) 3.66 (s, 3 H) 6.44 (d, J1.81 Hz, 1 H) 6.77 (dd, J15.32,9.30 Hz, 2 H) 7.30 – 7.41 (m, 2 H) 7.84 (dd, J=8.97, 2.23 Hz, 1 H) 8.21 (d, J=9.69 Hz, 1 H)8.36 (d, J=2.18 Hz, 1 H) 8.73 (d, J=1.76 Hz, 1 H) 11.65 (s, 1 H). m/z (ESI) 512.2 (M+H)t
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 460-37-7, its application will become more common.
Reference:
Patent; AMGEN INC.; WEISS, Matthew; MILGRAM, Benjamin C; MARX, Isaac E.; DINEEN, Thomas; (63 pag.)WO2017/106871; (2017); A1;,
Iodide – Wikipedia,
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