7-BROMO-1H-PYRIDO[2,3-B][1,4]OXAZIN-2(3H)-ONE Chemical Properties

Melting point:

247-251 °C(Solv: ethanol (64-17-5))

Boiling point:

398.8±42.0 °C(Predicted)

Density 

1.772±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

10.67±0.20(Predicted)

form 

solid

InChI

InChI=1S/C7H5BrN2O2/c8-4-1-5-7(9-2-4)12-3-6(11)10-5/h1-2H,3H2,(H,10,11)

InChIKey

UTPFXZJAASMEDW-UHFFFAOYSA-N

SMILES

O1CC(=O)NC2=CC(Br)=CN=C12

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

7-BROMO-1H-PYRIDO[2,3-B][1,4]OXAZIN-2(3H)-ONE Usage And Synthesis

Uses

7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one is an important chemical reagent that can be used to prepare heteroaryl compounds. The synthetic product can effectively inhibit necrosis and thus finds application in the treatment of diseases and conditions related to the necrosis pathway, including, for example, inflammation, tumors, metabolic diseases, and neurodegenerative diseases such as cerebral ischemia and stroke.

Synthesis

7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one is prepared by reacting 6-bromo-1H-pyrrolo[3,2-b]pyridine with pyridine and cyclohexyl carbonochloridate in anhydrous THF solution. The specific reaction process is as follows: To a solution of 6-bromo-1H-pyrrolo[3,2-b]pyridine (97 mg, 0.5 mmol) in anhydrous THF (5 mL) was added slowly pyridine (120 mg, 1.5 mmol) followed by cyclohexyl carbonochloridate (162 mg, 1 mmol) in THF (2 mL). The mixture was stirred at room temperature for 3 h. The reaction was quenched by the addition of saturated NaCl solution (20 mL). The aqueous phase was extracted with EtOAc (3×) and the combined organic layers were combined, dried and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 5/1) to give 7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one as a colorless oily liquid (120 mg, 75%).1H NMR (400 MHz, DMSO-d6) d 8.58 (s, 2H), 7.84 (d, J = 2.4 Hz, 1H), 8.77 (d, J = 3.6 Hz, 1H), 5.13-5.00 (m, 1H), 2.13-1.97 (m, 2H), 1.91-1.75 (m, 2H), 1.72- 1.33 (m, 6H).

7-BROMO-1H-PYRIDO[2,3-B][1,4]OXAZIN-2(3H)-ONE(105544-36-3)Related Product Information

• 7-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER
• 7-Bromo-1H-indazol-3-amine
• 7-BroMo-6-azaindole-3-carbaldehyde
• 7-BROMO-1H-INDOL-3-METHYLAMINE
• METHYL 7-BROMO-1H-INDAZOLE-3-CARBOXYLATE
• 3-HYDROXY-7-BROMO 1H-INDAZOLE
• Methyl 7-bromo-1H-indole-2-carboxylate
• 7-BROMO-1H-INDAZOLE-3-CARBOXYLIC ACID
• 2-amino-5-bromopyridin-3-ol
• 7-BROMO-1H-PYRIDO[2,3-B][1,4]OXAZIN-2(3H)-ONE
• 5-Bromo-2-ethoxypyridine
• 5-Bromo-2-methoxypyridine
• 2-Hydroxy-5-bromopyridine
• 1H-Pyrido[2,3-b][1,4]oxazin-2(3H)-one(9CI)
• 5-BROMO-2-METHOXY-3-CYANOPYRIDINE
• 2-(2-aminoethoxy)pyridine
• 7-bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
• 6-BROMO-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE