Reference of 107504-08-5 ,Some common heterocyclic compound, 107504-08-5, molecular formula is C6H4FNO2, 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.
A mixture of 14 (500 mg, 4 mmol) and LiAIH4(202 mg, 5 mmol) in THF (10 mL) was degassed and purged with N2for 3 times, and then the mixture was stirred at 0 C for 12 h under N2atmosphere. The reaction mixture was quenched by saturated sodium potassium tartrate (0.8 mL) at 15 C, and then filtered. The mixture was diluted with H20 (5 mL) and extracted with EtOAc (5 mL x 3). The combined organic layer was washed with brine (5 mL x 2), dried over Na2S04, filtered and concentrated under reduced pressure to give 15 (236 mg, 52%) as a yellow solid.1H NMR (400 MHz, DMSO-d6) 8.43 (d, J – 2.8 Hz, 1 H), 7.45-7.41 (m, 1 H), 7.31-7.27 (m, 1 H), 4.76 (s, 2H). A mixture of 15 (1 g, 8 mmol), DCC (3 g, 16 mmol), DMAP (96 mg, 786 umol) and A/-BOC-(S)-valine (2 g, 9 mmol) in DCM (5 mL) was degassed and purged with N2for 3 times, and then the mixture was stirred at 25 “C for 12 h under N2atmosphere. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02, PE/EtOAc = 5:1) to give 16 (1 .3 g, 51 %) as a yellow liquid.1H N R (400 MHz, DMSO-de) 8.55 (s, 1 H), 7.71-7.83 (m, 1 H), 7.54-7.51 (m, 1 H), 7.25 (d, J = 8.0 Hz, 1 H), 5.22-5.13 (m, 2H), 3.91 (t, J = 7.2 Hz, 1 H), 2.06-2.02 (m, 1 H), 1.38 (s, 9H), 0.87 (d, J – 6.4 Hz, 6H).
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. 107504-08-5, 5-Fluoro-2-picolinic acid, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; CARTER, David Scott; HALLADAY, Jason S.; JACOBS, Robert T.; LIU, Yang; PLATTNER, Jacob J.; ZHANG, Yong-Kang; WITTY, Michael John; (149 pag.)WO2017/195069; (2017); A1;,
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