Potassium Hydroxide → HCID 59375672, compound

Participants

Reaction Conditions

Reaction Steps

1-chloro-9-fluoro-6-isopropoxybenzo[c]-1,6-naphthyridine (107 mg, 0.368 mmol), potassium hydroxide (83.0 mg, 1.47 mmol), 2-di-t-butylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (31.3 mg, 0.0740 mmol), and Pd2(dba)3 (33.7 mg, 0.0370 mmol) were combined in a vial. 1,4-Dioxane (2.2 mL) and water (1.5 mL), were added, and the resulting suspension was degassed with argon for 10 min. The reaction mixture was heated to 100° C. and stirred for 16 h. After cooling to room temperature, the reaction mixture was added to saturated aqueous ammonium chloride (40 mL). The aqueous layer was extracted with ethyl acetate (2×40 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to a crude residue. The crude material was purified by preparative reverse phase HPLC eluting with an acetonitrile/water (with 0.05% TFA as a modifier) gradient, to afford 9-fluoro-6-isopropoxybenzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (500 MHz, DMSO-D6) δ 11.74 (s, 1H), 9.55 (d, 1H), 8.33 (dd, 1H), 7.53 (overlapping m, 2H), 6.56 (d, 1H), 5.64 (septet, 1H), 1.43 (d, 6H). LRMS (ESI) calc'd for (C15H13FN2O2) [M+H]+, 273.1; found 273.0.

Provenance & Evidence