反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 110 °C
PROCEDURE
实验过程
To a stirred, degassed mixture tert-butyl 3-(4-amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3-hydroxypiperidine-1-carboxylate (292 mg, 0.71 mmol), Intermediate C (355 mg, 1.06 mmol), Na2CO3 (225 mg, 2.13 mmol) and H2O (1 mL) in DMF (6 mL) was added tetrakis(triphenylphosphine)palladium(0) (82 mg, 0.071 mmol). The reaction was heated (110° C.) for 17 h and then cooled to rt. The mixture was partitioned between ethyl acetate (50 mL) and H2O (50 mL). The layers were separated and the aqueous layer was further extracted with ethyl acetate (1×50 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to dryness. The crude material was purified via ISCO® chromatography using a gradient of 50 to 75% ethyl acetate in hexanes to afford 270 mg (71%) of the desired product, which contained trace impurities. ES-MS m/z 540.30 [M+H]+, HPLC RT (min) 2.91.
WORKUP
后处理
- temperaturecooled to rt
- customThe mixture was partitioned between ethyl acetate (50 mL) and H2O (50 mL)
- customThe layers were separated
- extractionthe aqueous layer was further extracted with ethyl acetate (1×50 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated to dryness
- customThe crude material was purified via ISCO® chromatography