反应详情

To a solution of methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate (prepared as described in Example 1, Step 1) in dioxane (0.04 M) was added Na2CO3 (5 eq, 2 M aqueous solution), 3-formylfuran-2-boronic acid (1.4 eq) and bis(triphenylphosphine)palladium(II) dichloride (0.2 eq). The mixture was heated at reflux for 20 mins, at which point the heat was removed and the reaction cooled slightly to allow addition of a further 1 eq of boronic acid. The reaction was then heated for a further 1 h at reflux. Again, the reaction was cooled slightly to allow addition of a further 0.5 eq of boronic acid. After heating for a further 30 mins, the reaction was allowed to cool to RT, filtered and the filtrate diluted with EtOAc. The organic phase was washed with H2O and dried (Na2SO4) before being filtered and concentrated in vacuo. The crude was purified by flash chromatography (10-20% EtOAc/PE) to afford the title compound as an oil (38%); MS (ES+) m/z 466 (M+H)+, 488 (M+Na)+.

1. temperatureThe mixture was heated
2. temperatureat reflux for 20 mins, at which
3. customwas removed
4. temperaturethe reaction cooled slightly
5. temperatureThe reaction was then heated for a further 1 h
6. temperatureat reflux
7. temperatureAgain, the reaction was cooled slightly
8. temperatureAfter heating for a further 30 mins
9. filtrationfiltered
10. additionthe filtrate diluted with EtOAc
11. washThe organic phase was washed with H2O
12. dry with materialdried (Na2SO4)
13. filtrationbefore being filtered
14. concentrationconcentrated in vacuo
15. customThe crude was purified by flash chromatography (10-20% EtOAc/PE)