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To a flask charged with 8-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine (AAT Pharmaceuticals) (0.237 g, 1.547 mmol) was added THF (6.19 ml). The solution was cooled in an ice water bath prior to the addition of sodium hydride (60% in mineral oil) (0.068 g, 1.702 mmol). The resulting suspension was stirred for 30 min at 0° C., the 30 min at rt. The resulting pale yellow suspension was cooled in an ice water bath prior to the addition of 2-fluoro-5-(trifluoromethyl)benzonitrile (0.322 g, 1.702 mmol). The resulting mixture was stirred for 30 min at 0° C., then 1 hr at room temperature. The mixture was heated to 60° C. overnight then at reflux for 2 hr. The mixture was cooled to room temperature and added carefully to ice water and extracted with EtOAc (2×). The combined organics were dried with Na2SO4, filtered and dried under reduced pressure. The crude material was purified with a 25 g SNAP column ramping EtOAc in heptane (0-25%, 10% DCM throughout) yielding product, obtained as a yellow oil, 2-(8-fluoro-2H-benzo[b][1,4]oxazin-4(3 H)-yl)-5-(trifluoromethyl)benzonitrile (0.168 g, 0.521 mmol, 33.7% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.89-3.97 (m, 2 H) 4.36 (dd, J=4.94, 3.86 Hz, 2 H) 6.61 (dt, J=7.78, 1.79 Hz, 1 H) 6.70-6.80 (m, 2 H) 7.50 (d, J=8.80 Hz, 1 H) 7.71-7.77 (m, 1 H) 7.92-7.95 (m, 1 H). m/z (ESI) 323.1 (M+H)+.

1. temperatureThe solution was cooled in an ice water bath
2. customthe 30 min
3. customat rt
4. temperatureThe resulting pale yellow suspension was cooled in an ice water bath
5. stirringThe resulting mixture was stirred for 30 min at 0° C.
6. custom1 hr
7. customat room temperature
8. temperatureThe mixture was heated to 60° C. overnight
9. temperatureat reflux for 2 hr
10. temperatureThe mixture was cooled to room temperature
11. extractionextracted with EtOAc (2×)
12. dry with materialThe combined organics were dried with Na2SO4
13. filtrationfiltered
14. customdried under reduced pressure
15. customThe crude material was purified with a 25 g SNAP column
16. customyielding product