Sodium Carbonate → HCID 59375618, compound

Participants

Reaction Conditions

Reaction Steps

4-(cyclopropylethynyl)-9-bromo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (750 mg, 1.711 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (664 mg, 3.42 mmol), and PdCl2(dppf)-CH2Cl2 adduct (279 mg, 0.342 mmol) were added to a vial, followed by DMF (1.71E+04 μl) and aqueous sodium carbonate (2M) (1711 μl, 3.42 mmol). The reaction was purged with argon (subsurface bubbling) for 10 min. The reaction mixture was heated in a microwave oven at 130° C. for 45 min. The mixture was then cooled to room temperature and diluted with DMSO (˜17 mL) and filtered through a syringe filter (filter was rinsed with DMSO). This solution was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA. The fractions were combined, neutralized with NaHCO3 (sat) and extracted with dichloromethane (2×300 mL). The combined organics were washed with water (200 mL), brine (200 mL) dried over anhydrous sodium sulfate, swirled for 10 min with 1 g MP-TMT Pd scavenger resin, filtered and dried under reduced pressure to give the title compound as a yellow solid. 1H NMR (500 MHz, CD3OD) δ 13.10 (s, 1H), 11.28 (d, 1H, J=6.5 Hz), 10.02 (d, 1H, J=1.5 Hz), 8.49 (d, 1H, J=9.0 Hz), 8.28 (s, 1H), 7.96 (s, 1H), 7.83 (dd, 1H, J=8.5, 1.5 Hz), 7.49 (d, 1H, J=6.5 Hz), 7.45 (d, 1H, J=9.0 Hz), 4.87 (m, 1H), 1.53 (m, 1H) 1.21 (d, 3H, J=7 Hz), 0.98 (s, 9H), 0.88 (m, 2H), 0.72 (m, 2H). LRMS (ESI) calc'd for (C26H28N5O) [M+H]+, 426.2; found 426.2.

Provenance & Evidence