Lithium Chloride → 6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}-9-(1H-pyrazol-5-yl)benzo[c]-1,6-naphthyridin-1(2H)-one

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Reaction Conditions

Reaction Steps

To a solution of 9-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one (33 mg, 0.08 mmol) in DMF (1 mL) and sodium carbonate (0.5 mL, 2.0 M), were added lithium chloride (19.7 mg, 0.464 mg), 1H-pyrazol-5-ylboronic acid (17 mg, 0.16 mmol), and palladium tetrakis triphenylphosphine (27 mg). The mixture was degassed with nitrogen and heated in the microwave at 130° C. for 1 hr. The resulting black solution was filtered and purified by reverse phase HPLC to afford 6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}-9-(1H-pyrazol-5-yl)benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (600 MHz, CD3OD) δ 10.3 (s, 1H), 8.53 (d, 1H), 8.16 (d, 1H), 7.77 (s, 1H), 7.50 (d, 1H), 6.95 (s, 1H), 6.74 (d, 1H), 5.34 (m, 1H), 2.43 (m, 1H), 1.19 (d, 3H), 1.11 (d, 3H). LRMS (ESI) calc'd for (C20H19F3N5O) [M+H]+, 402.2; found 402.1.

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