Sodium Carbonate → (S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate

Participants

Reaction Steps

To a mixture of (S)-tert-butyl 1-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate (1.0 equiv.), 4-(benzyloxy)-2-chloropyrimidine (2.0 equiv.) and Pd(dppf)Cl2-DCM (0.15 equiv) in a 20 ml microwave vial, DME and 2M Na2CO3 were added (1.0 M). The vial was submitted to 125° C. for 20 min in microwave. The resulting mixture was partitioned between EtOAc and H2O. Upon separation, the organic layer was washed with NaCl(sat.), dried over Na2SO4, concentrated and purified by reverse-phase HPLC to yield (S)-tert-butyl 1-(6-(4-(benzyloxy)pyrimidin-2-yl)quinolin-4-yl)piperidin-3-ylcarbamate (88%). LC/MS=512.1 (M+H), LC=3.40 min.

Provenance & Evidence