5-Bromo-3-nitro-pyridin-2-yloxy)-acetic acid ethyl ester

Method I: 5-bromo-2-chloro-3-nitropyridine (100 mg, 0.42 mmol) and Ethyl glycolate (0.044 mL, 0.46 mmol) were dissolved in THF (5 mL) and cooled to 0°C. Sodium hydride (0.015 mL, 0.46 mmol) was added and the mixture was stirred for 1hr at room temperature. Reaction mixture was poured in ice water and extracted with EtOAc (2 x 10ml). The organiclayer was washed with brine (10ml), dried over sodium sulphate and concentrated. The crude product was purified by flash column using 100-200 silica gel to ethyl 2-(5-bromo-3-nitropyridin-2-yloxy)acetate (105 mg, 82 percent) 9(b). Step 1. Sodium hydride (55percent dispersion in mineral oil, 603 mg, 13.8 mmol) was added to a solution of ethyl glycolate (1.43 g, 13.8 mmol) in 1, 4-dioxane, and the reaction mixture was heated at 70° C. for 1 h, then 5-bromo-2-chloro-3-nitropyridine (Eur. Pat. Appl. EP 122109 (1984); 1.64 g, 6.91 mmol) was added, and stirring was continued at 70° C. for 1 h and at room temperature for 16 h. The reaction mixture was then neutralized with sat. aq. sodium hydrogencarbonate solution and extracted three times with dichloromethane. The organic layers were pooled, dried (NaTo a suspension of sodium hydride (5.31 g, 133 mmol) in 1 , 4-dioxane (250 ml), ethyl glycolate (12.56 ml, 133 mmol) was added drop wise over a period of 30 minutes ensuring that the temperature was maintained below 30°C. The resulting thick suspension was stirred at room temperature for 15 minutes. In a separate 11 round- bottomed flask was added 5-bromo-2-chloro-3-nitropyridine (21 g, 88 mmol) in 1 , 4- dioxane (150 ml) to give a brown solution. The suspension of sodium hydride and ethyl glycolate was added drop wise over a period of 30 minutes at 0°C. The resulting reaction mixture was heated to 80°C overnight. The reaction mixture was concentrated under reduced pressure and the crude residue was purified by Biotage silica chromatography (gradient 0percent to 10percent ethyl acetate in n- hexanes) to give the title compound (1 .8g, 44percent). N R (500 MHz, CDCI

Molecular Weight:305.08
XLogP3:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:303.96948
Monoisotopic Mass:303.96948
Topological Polar Surface Area:94.2
Heavy Atom Count:17
Complexity:283
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes