反应详情

温度

120 °C

tert-Butyl (R)-1-(4-bromophenyl)-4-((R)-3-(7-chloro-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate (31A) (0.111 mmol max, crude oil) and phenylboronic acid (0.144 mmol, 0.018 g) were added to a 5 mL microwave vessel equipped with a magnetic stir bar. Dioxane (2 mL) and Na2CO3 (1 mL of a 2 M in aqueous solution) were then added and the reaction vessel was flushed with nitrogen gas. PdCl2(dppf) (0.006 mmol, 0.004 g) was added, the reaction vessel was sealed and placed in a microwave reactor and heated to 120° C. for 15 minutes. The reaction solution was then poured into water, extracted with ethyl acetate, and washed once with saturated aqueous sodium chloride. The organic layer was collected and subsequently dried with anhydrous Na2SO4 and filtered. This filtrate was collected, concentrated, and dried in-vacuo. This crude material was directly purified by preparative LC/MS (gradient 25-85% CH3CN in H2O). The resultant fractions were collected and the solvent was removed in-vacuo affording tert-butyl (R)-1-(biphenyl-4-yl)-4-((R)-3-(7-chloro-1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate (31B) as a clear oil. ESI-MS: m/z 645.5 (M+H)+.

1. customequipped with a magnetic stir bar
2. customthe reaction vessel was flushed with nitrogen gas
3. customthe reaction vessel was sealed
4. customplaced in a microwave reactor
5. extractionextracted with ethyl acetate
6. washwashed once with saturated aqueous sodium chloride
7. customThe organic layer was collected
8. dry with materialsubsequently dried with anhydrous Na2SO4
9. filtrationfiltered
10. customThis filtrate was collected
11. concentrationconcentrated
12. customdried in-vacuo
13. customThis crude material was directly purified by preparative LC/MS (gradient 25-85% CH3CN in H2O)
14. customThe resultant fractions were collected
15. customthe solvent was removed in-vacuo