Application of 135450-23-6 ,Some common heterocyclic compound, 135450-23-6, molecular formula is C7H5ClN2, 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.
To a solution of commercially available chloride 30 (9.66 g,63.3 mmol) in DMF (400 mL) at ambient temperature was treatedwith potassium phthalimide (11.7 g, 63.3 mmol). After stirring for5 h, the mixture was concentrated under vacuum. The remainingmixture was taken up in H2O (200 mL) and was filtered to collectthe solid. The solid was washed with H2O (100 mL) and THF(100 mL) to obtain the desired phthalimide derivative (11.5 g,69%) and was moved forward without further purification. To asolution of the crude phthalimide derivative (5.84 g, 22.2 mmol)in THF/MeOH (200 mL, 1:1, v/v) at ambient temperature was treatedwith hydrazine monohydrate (1.18 mL, 24.4 mmol). After 2 h,1.0 M HCl (24.5 mL) was added to the mixture and was stirredfor another 3 h before concentrating the reaction mixture undervacuum. The remaining residue was taken up in H2O (200 mL)and the unwanted solid was removed through filtration. The filtratewas concentrated and placed under vacuum to remove theremaining H2O. The crude solid was taken up in CH2Cl2 (175 mL)and triethylamine (9.28 mL, 66.6 mmol) and Boc2O (4.86 g,24.4 mmol) was added. After stirring for 12 h at room temperature,the reaction was quenched with a saturated solution of NaHCO3(200 mL), extracted with CH2Cl2 (3 150 mL), dried over MgSO4,and concentrated under reduced pressure. The residue was purifiedusing flash chromatography (10-45% ethyl acetate in hexanes)to provided the aryl pyridine ?IN? fragment (2.24 g, 43%): 1H NMR(CDCl3, 400 MHz) d 7.78 (t, J = 7.6 Hz, 1H), 7.56 (d, J = 7.6 Hz, 1H),7.49 (d, J = 8.0 Hz, 1H), 5.51 (s, 1H), 4.44 (d, J = 5.6 Hz, 2H), 1.43(s, 9H); 13C NMR (CDCl3, 100 MHz) 160.1, 155.9, 137.6, 133.0,127.0, 125.1, 117.1, 79.9, 45.5, 28.3; IR (neat) 3347, 2979, 2934,2239, 1699, 1518, 1453, 1250, 1170, 862; HRMS (ESI) m/z calcdfor C12H15N3NaO3 [M+Na]+ 256.1062, found 256.1062.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135450-23-6, its application will become more common.
Reference:
Article; Clausen, Dane J.; Smith, William B.; Haines, Brandon E.; Wiest, Olaf; Bradner, James E.; Williams, Robert M.; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 5061 – 5074;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem