反应详情

温度

100 °C

To a solution of tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate (75 mg, 0.15 mmol) in toluene/ethanol (3 ml each), were added 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]azetidine (79 mg, 0.31 mmol), Pd(PPh3)4 (9 mg), and saturated sodium bicarbonate in water (300 ul). The reaction was degassed and heated to 100° C. for 18 hr under nitrogen gas. The mixture was poured to water, extracted with ethyl acetate (15 mL×3). The combined organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate: methanol=9:1:0.1 to 1:1:0.1) and again purified with HPLC (acetonitrile/water (0.05% formic acid), gradient, 25 ml/min) to give the product (6 mg, 8%). LCMS: 488 [M+H].

1. customThe reaction was degassed
2. additionThe mixture was poured to water
3. extractionextracted with ethyl acetate (15 mL×3)
4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
5. customevaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate: methanol=9:1:0.1 to 1:1:0.1)
7. customagain purified with HPLC (acetonitrile/water (0.05% formic acid), gradient, 25 ml/min)