Electric Literature of 66572-56-3 ,Some common heterocyclic compound, 66572-56-3, molecular formula is C6H4BrNO2, 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.
Stepl : 2-phenylisonicotinic acid 2-bromoisonicotinic acid (0.210 g, 1 .040 mmol) was dissolved in degassed DME (Volume: 8 ml) under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.060 g, 0.052 mmol) was added, the resulting reaction mixture was stirred for 15min.Then aqueous potassium carbonate (4.16 ml, 8.32 mmol) and phenylboronic acid (0.171 g, 1 .403 mmol) were added subsequently. The resulting RM was refluxed at 95 C for 18h and then cooled to rt. After filtration over celite the reaction mixture was acidified to pH 3-4 and the white precipitate was filtered off and washed with water. This resulted in a white powder after recrystallization from 2-methoxyethanol. Yield: 0.1 06 g, 57%. 1 H NMR (400 MHz, DMSO-c): delta 7.44 – 7.60 (m, 3H), 7.71 – 7.86 (dd, J = 4.9, 1 .5 Hz, 1 H), 8.05 – 8.19 (m, 2H), 8.23 – 8.35 (t, J = 1 .2 Hz, 1 H), 8.79 – 8.93 (dd, J = 5.1 , 0.8 Hz, 1 H), 13.56 – 13.97 (s, 1 H). UPLC I (ESI) Rt 1 .37 min, m/z 200.5 [M+H]+ (92%). – –
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. 66572-56-3, 2-Bromoisonicotinic acid, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; UNIVERSITEIT ANTWERPEN; FOX CHASE CANCER CENTER; JANSEN, Koen; DE MEESTER, Ingrid; HEIRBAUT, Leen; CHENG, Jonathan D; JOOSSENS, Jurgen; AUGUSTYNS, Koen; VAN DER VEKEN, Pieter; WO2013/107820; (2013); A1;,
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