반응 #775
ord-afb4a5c3ac0340ae885e81e91d7c667d
반응 조건
실험 절차
**_September 28 2015_** 4-methylthiazol-2-amine (300 mg, 2.63 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (676 mg, 2.63 mmol), 3-(6-bromopyridin-2-yl)-1,3-oxazinan-2-one (676 mg, 2.63 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (152 mg, 0.26 mmol) and cesium carbonate (1027 mg, 3.15 mmol) in toluene (13 mL)/DMF (2.00 mL) were microwaved at 115 °C under N2 for one hour. (Note: Based on the observation in EN07946-41, _DMF was added to improve the heating due to the low thremal absorbance of toluene.)_ One hour later, LCMS showed 13% of the precursor MH+257/259 @ 0.84 min and 36% of the desired mass MH+291 @ 0.86 min along with some unknowns on a 2-min basic run. The reaction seemed not complete. The reaction was microwaved at 115 °C for another 45 min. One hour and 45 min later, LCMS showed 7% of the precursor MH+257/259 @ 0.84 min and 37% of the desired mass MH+291 @ 0.86 min along with some unknowns on a 2-min basic run. The reaction seemed stuck, and was cooled to RT. **_September 29 2015_** The reaction mixture was diluted with EtOAc, washed with water, filtered, and evaporated to give a brown solid as the crude product. The crude product was added to a Biotage column, and was eluted with 15-100%EtOAc in Heptane. Collected fractions. **_September 30 2015_** Based on TLC and LCMS, the product fractions were combined, and evpoarated to give an yellow-brown solid, which was vacuumed overnight at 40 °C **_OCtober 1 2015_** Based on LCMS, it was 100% pure; based on NMR, it was 90~95% pure, and contained 0.1eq of DMF.