Sodium Carbonate → methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-phenyl-1H-indole-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate in dioxane (0.06 M) was added bis(triphenylphosphine)palladium(II) dichloride (0.2 eq) at RT under a nitrogen atmosphere. Then aqueous Na2CO3 (2 M; 4 eq) followed by phenylboronic acid (2.5 eq) were added and the reaction was heated to 80° C. for 2 h. The reaction mixture was allowed to cool and concentrated in vacuo. DCM was added and the organic phase washed with H2O, brine and dried over Na2SO4 before being filtered and concentrated in vacuo. The crude material was purified by automated FC (SiO2; 95:5 EtOAc/PE) to afford the title compound (88%). (ES+) m/z 448 (M+H)+

Provenance & Evidence