反应详情

温度

100 °C

To a suspension of 3-bromo-2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.250 g, 1 eq.) in a mixture of toluene (5 mL), ethanol (5 mL), and saturated sodium bicarbonate (1 mL) was added (4-(((tert-butoxycarbonyl)amino)methyl)phenyl)boronic acid (0.1 g, 1.5 eq.). The reaction was degassed (nitrogen) for 5 minutes and tetrakis(triphenylphosphine)palladium(0) added (0.025 g). The reaction was again degassed for 5 minutes and stirred at 100° C. overnight. The reaction mixture was cooled to room temperature and poured onto water (50 mL). The aqueous phase was extracted with dichloromethane (2×50 mL) and the organic extracts were combined and washed with water (1×50 mL), brine (1×50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (25-75% ethyl acetate in hexanes) gave the product which was triturated with ether to give tert-butyl 4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)benzylcarbamate (0.133 g, 40%). LCMS: 516 [M+H].

1. customThe reaction was degassed (nitrogen) for 5 minutes
2. additiontetrakis(triphenylphosphine)palladium(0) added (0.025 g)
3. customThe reaction was again degassed for 5 minutes
4. temperatureThe reaction mixture was cooled to room temperature
5. additionpoured onto water (50 mL)
6. extractionThe aqueous phase was extracted with dichloromethane (2×50 mL)
7. washwashed with water (1×50 mL), brine (1×50 mL)
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customPurification by column chromatography (25-75% ethyl acetate in hexanes)
12. customgave the product which
13. customwas triturated with ether