Sodium Carbonate → 3-[6-isopropyl-9-(1-methyl-1H-pyrazol-4-yl)-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl]prop-2-ynamide

Participants

Reaction Conditions

Reaction Steps

3-(9-bromo-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl)prop-2-ynamide (57 mg, 0.15 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (62 mg, 0.30 mmol), and PdCl2(dppp-CH2Cl2 adduct (24 mg, 0.030 mmol) were added to a vial, followed by DMF (1.8 ml) and aqueous sodium carbonate (2M) (0.15 ml, 0.30 mmol). The resulting suspension was purged with argon (subsurface bubbling) for 10 min, then heated in a microwave reactor at 100° C. for 30 min. The mixture was cooled, diluted with DMF, and filtered to remove salts. The solution was purified directly by preparative reverse phase HPLC eluting with an acetonitrile/water (with 0.05% TFA as a modifier) gradient, to afford 3-[6-isopropyl-9-(1-methyl-1H-pyrazol-4-yl)-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl]prop-2-ynamide. 1H NMR (500 MHz, DMSO-D6) δ 12.15 (br s, 1H), 10.15 (s, 1H), 8.46 (d, 1H), 8.34 (s, 1H), 8.01-7.98 (overlapping m, 3H), 7.89 (br s, 1H), 7.56 (br s, 1H), 4.08 (septet, 1H), 3.92 (s, 3H), 1.41 (d, 6H). LRMS (ESI) calc'd for (C22H19N5O2) [M+H]+, 386.2; found 386.1.

Provenance & Evidence