4-Fluorobenzylamine → HCID 69812440, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 4-fluoro-benzylamine (54 mg, 0.43 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (8 mg, 0.02 mmol), and sodium tert-butoxide (63 mg, 0.65 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered through a filter membrane, and purified via prep-LC-MS. The recovered product was converted to the HCl salt via suspending in CH2Cl2, addition of 2 M HCl/ether, filtering the resulting precipitate, and washing with CH2Cl2 to provide 39 (5 mg, 6% yield) as a yellow solid. LC-MS (M+H=320, obsd.=320). 1H NMR (400 MHz, d6-DMSO): δ 11.65 (s, 1H), 8.38 (d, 1H), 8.29 (d, 1H), 8.04 (d, 1H), 7.88 (m, 2H), 7.64 (m, 1H), 7.49 (m, 2H), 7.14 (m, 2H), 4.42 (s, 2H).

Provenance & Evidence