3-CHLORO-4-NITROPYRIDINE

When in the procedure of Example 1, equal molar amounts of the following are substituted for 2-chloro-3-nitropyridine, 2-chloro-5-methoxy-3-nitropyridine, 3-chloro-4-nitropyridine, 5-chloro-2-methoxy-4-nitropyridine, 4-chloro-3-nitropyridine, and 3-chloro-2-nitropyridineWhen in accordance with the procedure of example 1, equal molar amounts of the following are substituted for 2-chloro-3-nitropyridine: 2-chloro-3-nitro-5-methoxypyridine, 3-chloro-4-nitropyridine, 2-methoxy-4-nitro-5-chloropyridine, 3-nitro-4-chloropyridine, and 2-nitro-3-chloropyridine, General procedure: In a glovebox, K3PO4 (10 mol %, 5.3 mg), 18-Crown-6 (20 mol %, 13.2 mg) , and 2.5 mL tetrahydrofuran were added into a Schlenk tube equipped with a stir bar, then thiol (0.25 mmol) and nitrobenzene derivative (0.25 mmol) were added on the outside under an air atmosphere. The reaction mixture was stirred at room temperature 3 h (450 rpm). The resultant solution was concentrated and purified by silica gel column chromatography with EtOAc and petroleum ether as the eluent to give the corresponding thioether. (5 g, 31.63 mmol), 4-pyridine boronic acid (3 g, in a 500 ml one-neck flask).37.75mmol), 50 ml of a 2 M potassium carbonate aqueous solution was dissolved in 50 ml of ethanol and 100 ml of toluene in a solvent.Under the protection of N2, PdCl2(PPh3)2 (0.75 g, 0.98 mmol) was added. The temperature was slowly raised to 100 C, and the mixture was reacted under reflux for 24 h.After cooling, the layers were separated, and the organic layer was evaporated, and then, with petroleum ether and ethyl acetate (1.5:1).4.5 g of a pale yellow solid were obtained in a yield of 65%.

Molecular Weight:158.54
XLogP3:1.3
Hydrogen Bond Acceptor Count:3
Exact Mass:157.9883050
Monoisotopic Mass:157.9883050
Topological Polar Surface Area:58.7
Heavy Atom Count:10
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes