Related Products of 55899-13-3 ,Some common heterocyclic compound, 55899-13-3, molecular formula is C14H17BrN2O3S, 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.
The reaction was performed using general flow procedure reacting 3-bromopyridine 2a with ethylpropiolate 4b. The outlet solution (195 mL, collected over 51 mins) was stirred at room temperature whiletriethylamine (17.5 mL, 126 mmol) was added followed by ethyl propiolate (9.30 mL, 98.4 mmol). The bright redmixture was stirred at room temperature for 15 minutes was concentrated in vacuo to remove the MeCN and thendiluted with EtOAc (250 mL) and brine (100 mL). The organic layer was separated and the aqueous phase washedtwice more with EtOAc (2 x 200 mL). The combined organic layers were dried over anhydrous sodium sulfate andconcentrated in vacuo to give a dark red oil.The crude material was purified by column chromatography on a 100 g silica column using the Biotage machine anda gradient from 7 to 60 % EtOAc/heptane. 5c eluted first from the column. Pale red solid (1.94 g, 51 min collectiontime, 11 %). 1H NMR (400 MHz, d6-DMSO) (3H, t, J = 4 Hz, CH2CH3), 4.31 (2H, q, J = 4 Hz, CH2CH3), 7.743 SYNLETT: LETTERTemplate for SYNLETT and SYNTHESIS Thieme Stuttgart · New York 2017-04-25 page 3 of 4(1H, d, J = 8 Hz, ArH), 8.01 (1H, d, J = 4 Hz, ArH), 8.47 (1H, s, ArH), 9.31 (1H, s, ArH) ppm. 13C NMR (101 MHz,d6-DMSO) 14.3, 59.8, 103.6, 108.1, 118.9, 130.3, 131.3, 138.6, 144.7, 162.2 ppm. HRMS (FAB) calcd forC10H10O2N2Br 268.99202, found 268.99194/270.98981
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. 55899-13-3, 1-Amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Brocklehurst, Cara E.; Koch, Guido; Rothe-Poellet, Stephanie; La Vecchia, Luigi; Synlett; vol. 28; 13; (2017); p. 1636 – 1640;,
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