4,6-dichloro-2(2H)-Pyridinone

2, 4-Dichloro-6-hydroxypyridine; Sodium nitrite (64 mg, 0.93 mmol) dissolved in water (0.6 mL), was added dropwise to a stirred solution of 2-amino-4, 6-dichloropyridine (prepared according to the method described in Recl. Trav. Chim. Pays-Bas, 1950, 69, 673) (126 mg, 0.77 mmol) in 5percent sulphuric acid (aq) (5 mL) at 0° C., over 5 min. The mixture was stirred at 0° C. for 1 h and then diluted with water (20 mL) and extracted with DCM (3.x.20 mL). The combined extracts were washed with brine (20 mL), dried over MgSOSodium nitrite (64mg, 0.93mmol) dissolved in water (0.6 ml.) was added dropwise to a stirred solution of 2-amino-4, 6-dichloropyridine (prepared according to the method described in Reel. Trav. Chim. Pays-Bas, 1950, 69, 673) (126 mg, 0.77 mmol) in 5percent sulphuric acid (5 ml.) at 0 °C, over 5 min. The mixture was stirred at 0 °C for 1 h and then diluted with water (20 ml.) and extracted with dichloromethane (3 x 20 ml_). The combined extracts were washed with brine (20 ml_), dried (MgSOSodium nitrite (64 mg, 0.93 mmol) dissolved in water (0.6 mL) was added dropwise to a stirred solution of 2-amino-4, 6-dichloropyridine (prepared according to the method described in Recl. Trav. Chim. Pays-Bas, 1950, 69, 673) (126 mg, 0.77 mmol) in 5percent sulphuric acid (5 mL) at 0 C., over 5 min. The mixture was stirred at 0 C. for 1 h and then diluted with water (20 mL) and extracted with dichloromethane (3 20 mL). The combined extracts were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo to afford the product as an orange solid (116 mg, 92percent).Data for 2, 4-dichloro-6-hydroxypyridine: MS (ESI) m/z:164/166 ([M+H]+).Sodium nitrite (64mg, 0.93mmol) dissolved in water (0.6 ml_), was added dropwise to a stirred solution of 2-amino-4, 6-dichloropyridine (prepared according to the method described in Reel. Trav. Chim. Pays-Bas, 1950, 69, 673) (126 mg, 0.77 mmol) in 5percent sulphuric acid (aq) (5 ml.) at 0 °C, over 5 min. The mixture was stirred at 0°C for 1 h and then diluted with water (20 ml.) and extracted with DCM (3 x 20 ml_). The combined extracts were washed with brine (20 ml_), dried over MgSO2, 4-Dichloro-6-hydroxypyridine; Sodium nitrite (64 mg, 0.93 mmol) dissolved in water (0.6 mL), was added dropwise to a stirred solution of 2-amino-4, 6-dichloropyridine (prepared according to the method described in Recl. Trav. Chim. Pays-Bas, 1950, 69, 673) (126 mg, 0.77 mmol) in 5percent sulphuric acid (aq) (5 mL) at 0° C., over 5 min. The mixture was stirred at 0° C. for 1 h and then diluted with water (20 mL) and extracted with DCM (3.x.20 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4 and concentrated in vacuo to afford the Sodium nitrite (64mg, 0.93mmol) dissolved in water (0.6 ml.) was added dropwise to a stirred solution of 2-amino-4, 6-dichloropyridine (prepared according to the method described in Reel. Trav. Chim. Pays-Bas, 1950, 69, 673) (126 mg, 0.77 mmol) in 5percent sulphuric acid (5 ml.) at 0 °C, over 5 min. The mixture was stirred at 0 °C for 1 h and then diluted with water (20 ml.) and extracted with dichloromethane (3 x 20 ml_). The combined extracts were washed with brine (20 ml_), dried (MgSO4) and concentrated in vacuo to afford the product as an orange solid (116 mg, 92 percent).Data for Sodium nitrite (64 mg, 0.93 mmol) dissolved in water (0.6 mL) was added dropwise to a stirred solution of 2-amino-4, 6-dichloropyridine (prepared according to the method described in Recl. Trav. Chim. Pays-Bas, 1950, 69, 673) (126 mg, 0.77 mmol) in 5percent sulphuric acid (5 mL) at 0 C., over 5 min. The mixture was stirred at 0 C. for 1 h and then diluted with water (20 mL) and extracted with dichloromethane (3 20 mL). The combined extracts were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo to afford the product as an orange solid (116 mg, 92percent).Data for Sodium nitrite (64mg, 0.93mmol) dissolved in water (0.6 ml_), was added dropwise to a stirred solution of 2-amino-4, 6-dichloropyridine (prepared according to the method described in Reel. Trav. Chim. Pays-Bas, 1950, 69, 673) (126 mg, 0.77 mmol) in 5percent sulphuric acid (aq) (5 ml.) at 0 °C, over 5 min. The mixture was stirred at 0°C for 1 h and then diluted with water (20 ml.) and extracted with DCM (3 x 20 ml_). The combined extracts were washed with brine (20 ml_), dried over MgSO4 and concentrated in vacuo to afford the 2, 4-Dichloro-6-hydroxypyridine (696 mg, 4.2 mmol), 3-exo-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (965 mg, 4.2 mmol) and (4, 4-Dimethyl-1, 1-dioxido-1, 2, 5-thiadiazolidin-2-yl)triphenylphosphonium (4.31 g, 10.5 mmol) in THF (20 mL) were stirred for 16 h. Ethyl acetate (50 mL) and water (20 mL) were added and the organic and aqueous layers were separated. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was then purified by chromatography on silica gel. Elution with 10:90 ethyl acetate:heptane afforded 3-exo-(4, 6-dichloropyridin-2-yloxy)-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (1.29 g, 3.6 mmol, 82percent).2, 4-Dichloro-6-hydroxypyridine (696mg, 4.2mmol), 3-exo-hydroxy-8- azabicyclo[3.2.1]octane-8-carboxylic acid terf-butyl ester (965mg, 4.2mmol) and (4, 4- Dimethyl-1 , 1-dioxido-1 , 2, 5-thiadiazolidin-2-yl)triphenylphosphonium (4.31g, 10.5mmol) in THF (2OmL) were stirred for 16h. Ethyl acetate (5OmL) and water (2OmL) were added and the organic and aqueous layers were separated. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was then purified by chromatography on silica gel. Elution with 10:90 ethyl acetate:heptane afforded 3-exo-(4, 6-dichloropyridin-2- yloxy)-8-azabicyclo[3.2.1]octane-8-carboxylic acid terf-butyl ester (1.29g, 3.6mmol, 82percent). M.S. (ESI) m/z: 373, 375 [M+H]+.

Molecular Weight:163.99
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:162.9591691
Monoisotopic Mass:162.9591691
Topological Polar Surface Area:29.1
Heavy Atom Count:9
Complexity:207
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes