Bromide ion → 3,4-Dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,8-naphthyridine-1(2h)-carboxamide

Participants

Reaction Steps

To a solution of crude 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (175 mg, 0.63 mmol) in MeCN (9.0 mL) is added bromide 2 (1.0 eq.) and saturated aqueous Na2CO3 solution (4.0 mL). Then Pd(dppf)Cl2 (23 mg, 0.031 mmol) is added under N2 atmosphere and the mixture is microwaved at 120° C. The progress of the reaction is monitored and after the reaction is completed, the solid is filtered and the filtrate is concentrated. The residue is partitioned between DCM and water. The organic layer is separated and washed with water and brine, dried over Na2SO4 and concentrated to give the crude product. Purification by column chromatography affords the desired product.

Provenance & Evidence