Related Products of 914358-72-8 ,Some common heterocyclic compound, 914358-72-8, molecular formula is C6H5BrClN, 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.
Example 60(1r,4r)-6′-(5-Chloro-6-methylpyridin-3-yl)-4-methoxy-5”-methyl-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine; 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi(1,3,2-dioxaborolane) (287 mg, 1.13 mmol), (1r,4r)-6′-bromo-4-methoxy-5”-methyl-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine (Example 19, 213 mg, 0.57 mmol) and potassium acetate (167 mg, 1.70 mmol) and dioxane (3 mL) were added and the mixture was degassed with a stream of argon (g) for a couple of min. PdCl2(dppf) CH2Cl2 (32.4 mg, 0.04 mmol) was added and the mixture was heated to reflux for 1.5 h under N2 atmosphere. 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi(1,3,2-dioxaborolane) (120 mg, 0.47 mmol) was added and the reaction was heated to reflux overnight. The volatiles were removed in vacuo and 80 mg of the residue ((1r,4r)-4-methoxy-5”-methyl-6′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine (MS (ES+) m/z 424 [M+H]+) was mixed with 5-bromo-3-chloro-2-methylpyridine (Intermediate 43, 47 mg, 0.23 mmol), K2CO3 (0.38 mL, 0.76 mmol) and dioxane (2 mL). The mixture was degassed with a stream of argon (g) for a couple of min. PdCl2(dppf) CH2Cl2 adduct (138 mg, 0.19 mmol) was added. The vial was sealed and heated in a microwave reactor at 140 C. for 30 min. EtOAc was added and the mixture was washed with brine and water. The organic phase was dried with MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (12 g SiO2, 0-20% MeOH containing 0.1 M NH3 in DCM). The crude product was purified with preparative chromatography. The fractions containing product were combined and concentrated. The water phase was extracted with DCM and the phases were separated using a phase separator. The organic phase was concentrated in vacuo yielding the title compound (5 mg, 6% yield): 1H NMR (CD3OD) delta ppm 1.11 (td, 1H), 1.24-1.43 (m, 2H), 1.49 (td, 1H), 1.63 (td, 2H), 1.90-2.00 (m, 2H), 2.32 (s, 3H), 2.61 (s, 3H), 3.04-3.12 (m, 1H), 3.15 (d, 1H), 3.25 (d, 1H), 3.33 (s, 3H), 6.99 (d, 1H), 7.47 (d, 1H), 7.55 (dd, 1H), 7.99 (d, 1 H), 8.51 (d, 1H); MS (MM-ES+APCI)+ m/z 423 [M+H]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,914358-72-8, its application will become more common.
Reference:
Patent; ASTRAZENECA AB; US2012/165347; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem