Sodium Carbonate → 6-isopropyl-9-(1-methyl-1H-pyrazol-4-yl)benzo[c]-1,6-naphthyridin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one (50 mg, 0.16 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (66 mg, 0.32 mmol), PdCl2(dppf)-CH2Cl2 adduct (26 mg, 0.032 mmol), DMF (1.7 ml), and 2 M aqueous sodium carbonate (0.16 ml, 0.32 mmol) were combined in a microwave vial and sparged with argon for 5 minutes. The reaction mixture was heated in a microwave reactor at 100° C. for 30 min. The reaction mixture was diluted with MeOH and purified directly by preparative reverse phase HPLC eluting with an acetonitrile/water (with 0.05% TFA modifier) gradient to afford 6-isopropyl-9-(1-methyl-1H-pyrazol-4-yl)benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (500 MHz, DMSO D-6) δ 11.69 (br d, 1H), 10.20 (d, 1H), 8.42 (d, 1H), 8.32 (s, 1H), 7.97 (s, 1H), 7.94 (dd, 1H), 7.51 (t, 1H), 6.73 (d, 1H), 4.06 (septet, 1H), 3.92 (s, 3H), 1.37 (d, 6H). LRMS (ESI) calc'd for (C19H18N4O) [M+H]+, 319.1; found 319.1.

Provenance & Evidence