7-bromoquinoxalin-2(1H)-one

To a solution of quinoxalin-2(lH)-one (54.64 g, 374 mmol, 1.0 eq.) in HOAc (1000 mL) was added a solution of BrTo a solution of quinoxalin-2(1H)-one (54.64 g, 374 mmol, 1.0 eq.) in HOAc (1000 mL) was added a solution of BrPreparation of -(3-fluorophenyl)-3-(3-((3-morpholinoquinoxalin-6-yl)oxy)phenyl)urea 1 -(3-fluorophenyl)-3-(3-((3-morpholinoquinoxalin-6-yl)oxy)phenyl)urea [0186] To a solution of quinoxalin-2(lH)-one (54.64 g, 374 mmol, 1.0 eq.) in HOAc (1000 mL) was added a solution of Br[0174] To a solution of quinoxalin-2(lH)-one (54.64 g, 374 mmol, 1.0 eq.) in HOAc (1000 mL) was added a solution of BrExample 69: 3-oxo-3., 4-dihvdro-2H-benzo[l, 41thiazine-6-carboxylic acid {l-[2-(7- methylsulfanyl-quinoxalin-2-yloxy)-ethyll-piperidin-4-yl}-amide: Preparation of 7-bromo-iH-quinoxalin-2-one: Bromine (7.36 mL, 147 mmol, 1.05 eq) is added at room temperature to a stirred suspension of iH-quinoxalin-2-one (20 g, 137 mmol, 1.0 eq) in acetic acid (400 mL). After 48 hours stirring at room temperature, the reaction mixture is poured into ice (500 mL) and the resulting precipitate is collected by filtration, washed with water and ethyl acetate to afford7-bromo-iH-quinoxalin-2-one as a yellow solid (29.4 g, 73percent yield). Step B: Preparation of 7-bromo-1H- uinoxalin-2-oneTo a stirred solution of 1 H-quinoxalin-2-one (50 g, 342.5 mmol) in glacial acetic acid (2500 ml.) was added bromine (54.7 g, 342.5 mmol in 120 ml_ acetic acid) over a period of 1.5 h at rt. After 18 h stirring, the mixture was slowly poured into 2000 ml_ water and stirred for 1 h at rt. The precipitate was filtered and the residue was washed with water and dried to give 7-bromo-1 H- quinoxalin-2-one as an off-white solid (51 g, 66percent): To a cooled 0 °C solution of quinoxalin-2(1 /-/)-one (I-70) (50 g, 342.2 mmol) in acetic acid (800 ml_) was added in a dropwise manner a solution of bromine (32 ml_) in acetic acid (200 ml_) over a period of 30 min. Solids formed within the reaction upon addition of bromine, and the reaction was allowed to stir slowly for a further 90 min. The solid was filtered, washed with MeOH and ether, and dried under high vacuum to afford 7-bromoquinoxalin-2(1 /-/)-one (1-71) (45 g, 58percent) as a white solid. LCMS (APCI), m/z 224.1 [M + H]+; 1H NMR (400 MHz, DMSO-c/6J 8 ppm 12.46 (s, 1 H), 8.16 - 8.18 (m, 1 H), 7.69 - 7.72 (d, 1 H), 7.44 - 7.46 (m, 2 H).Bromine (3.56 mL, 68.63 mmol) was slowly added to a solution of quinoxalin-2(lH)-one (10.03 g, 68.63 mmol) in 0.1M acetic acid (686.3 mL). The reaction mixture was stirred at ambient temperature for 1.5 hours. The resulting solids were collected by filtration and washed with hexanes to afford 7-bromoquinoxalin-2(lH)-one (4.02 g, 17.86 mmol, 26.0percent yield). 1H NMR (400 MHz, (CD

Molecular Weight:225.04
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:223.95853
Monoisotopic Mass:223.95853
Topological Polar Surface Area:41.5
Heavy Atom Count:12
Complexity:229
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes