With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.category: pyridine-derivatives
(Step 6) Preparation of 8-(6-tert-butyl-1H-benzo[d]imidazol-2-yl)-4-(5-methoxypyridin-2-yl)-3,4-dihydro-2H-benzo[b][1,4-]oxazine To a solution of 4-(5-tert-butyl-1H-benzo[d]imidazol-2-yl)benzene amine 3.1 g (10 mmol) in toluene 10 mL were added 2-chloro-5-methoxy pyridine 1.5 g (10 mmol), Pd(OAc)2 0.1 g (0.5 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 0.5 g (0.8 mmol) and Cs2CO3 4.6 g (14 mmol), followed by stirring at 90 C. for 12 hrs. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and diluted with ethylacetate. The product thus formed was washed with a saturated sodium bicarbonate solution and a saturated NaCl solution, dried over magnesium sulfate and concentrated in a vacuum. The residue was purified by column chromatography (developing solvent: ethylacetate/hexane=2/3) to give 3.5 g of the title compound (yield 85%). 1H NMR (MeOD-d4) delta: 8.04 (d, 1H, J=3.0 Hz), 7.79 (dd, 2H, J=7.8, 1.5 Hz), 7.67 (d, 1H, J=1.7 Hz), 7.56 (d, 1H, J=8.6 Hz), 7.38 (m, 2H), 7.25 (d, 1H, J=9.0 Hz), 7.17 (dd, 1H, J=8.1, 1.4 Hz), 6.95 (t, 1H, J=8.0 Hz), 4.52 (t, 2H, J=4.4 Hz), 3.99 (t, 2H, J=4.4 Hz), 3.86 (s, 3H), 1.41 (s, 9H)
At the same time, in my other blogs, there are other synthetic methods of this type of compound,139585-48-1, 2-Chloro-5-methoxypyridine, and friends who are interested can also refer to it.
Reference:
Patent; Daewoong Pharmaceutical Co., Ltd.; US8026235; (2011); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem