7-bromo-1H,2H,3H,5H-pyrido(2,3-e)(1,4)oxazepin-2-one → 7-bromo-1H,2H,3H,5H-pyrido[2,3-e][1,4]oxazepine

Temperature

0 °C

To a solution of 3-Bromo-5,9-dihydro-6-oxa-1,9-diazabenzocyclohepten-8-one (1.0 g, 4.13 mmol) in THF (40 mL) at 0° C. was added BH3 (30 mL of a 1.0 M solution in THF, 30.0 mmol). The solution was heated to reflux. After 18 h, the solution was cooled to 0° C. and the reaction quenched with H2O (2.5 mL). The mixture was concentrated and the resulting off-white solid was dissolved in MeOH (30 mL) and NaOH (15 mL of a 2 N solution). The mixture was heated at reflux for 4 h. The MeOH was removed under reduced pressure. The resulting precipitate was collected by filtration and washed with H2O (20 mL). The white solid was dried to give the title compound (0.360 g, 38%). 1H NMR (300 MHz, DMSO-d6) δ 8.06 (d, J=2.3 Hz, 1H), 7.71 (d, J=2.3 Hz, 1H), 6.55 (br s, 1H), 4.47 (s, 2H), 3.74-3.70 (m, 2H), 3.16-3.12 (m, 2H); ESI MS m/z 229 (100%); 231(100%)[C8H9BrN2O+H]+.

1. temperatureThe solution was heated to reflux
2. customthe reaction quenched with H2O (2.5 mL)
3. concentrationThe mixture was concentrated
4. dissolutionthe resulting off-white solid was dissolved in MeOH (30 mL)
5. temperatureThe mixture was heated
6. temperatureat reflux for 4 h
7. customThe MeOH was removed under reduced pressure
8. filtrationThe resulting precipitate was collected by filtration
9. washwashed with H2O (20 mL)
10. customThe white solid was dried

ORD record

ord-2712bb50ee884cfabe9a8ed888ba5c07

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318720B2