4-CHLORO-2-METHOXY-PYRIDINE

(d) 50.6 mL of isopropyl magnesium chloride (2 mol/L tetrahydrofuran solution) was cooled with ice, and a solution having 19.8 g (84.3 mmol) of the crude product of 4-iodo-2-methoxypyridine obtained in step (c) dissolved in 80 mL of tetrahydrofuran, was added, followed by stirring at 0°C for 1 hour and at room temperature for 1 hour. Then, 16.9 g (127 mmol) of N-chlorosuccinimide was gradually added, followed by stirring at room temperature for 1 hour. 100 mL of water was added to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. Extraction with ethyl ether was carried out, then the organic layer was dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 11.0 g (crude yield 91percent) of a crude product of 4-chloro-2-methoxypyridine.1H-NMR(CDCl3, 400 MHz) : δ (ppm) = 3.91(s, 3H), 6.70(d, 1H, J = 2.0 Hz), 6.81(dd, 1H, J = 6.0 Hz, 2.0 Hz), 7.99(d, 1H, J = 6.0 Hz)[1035] To a mixture of compound 1 (68 g, 0.465 mol) in toluene (250 mL) was added CuI (17.9 g, 0.093 mol), (MeTo a mixture of compound 1 (68 g, 0.465 mol) in toluene (250 mL) was added CuT (17.9 g, 0.093mo1), (Me2NHCH2)2 (36.8 g, 0.418 mol) and NaOMe (50.2 g 0.93 mol). The mixture was purged with nitrogen for three times and then heated at 100°C for 8 hours. The mixture was concentrated to remove toluene, diluted with H20 and extracted with EtOAc. After standard workup, the crude product was chromatographed on silica gel (PE) to give compound 2 (39.5 g, 60percent yield).4-Chloro-2-hydroxy-pyridine (247 mg, 1.91 mmol), AgUnder a nitrogen atmosphere, nickel bromide (4.4 mg, 0.02 mmol), 4, 4'-dimethoxy-2, 2'-bipyridine (4.3 mg, 0.02 mmol), magnesium chloride (28.6 mg, 0.3 mmol), manganese powder (43.95 mg, 0.8 mmol), and a solvent NMP (0.5 mL) was added )And stir well. Weigh To a solution of LDA (1.0 M solution in hexane) (29.3 mL, 29.3 mmol) in THF (45 mL) was added a solution of

Molecular Weight:143.57
XLogP3:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:143.0137915
Monoisotopic Mass:143.0137915
Topological Polar Surface Area:22.1
Heavy Atom Count:9
Complexity:89.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes