Ethyl Acetate → 5-(7-Chloro-2-methyl-1,6-naphthyridin-3-yl)-2-fluoro-4-methylaniline

Participants

Reaction Conditions

Reaction Steps

Sparge a mixture of 7-chloro-2-methyl-1,6-naphthyridin-3-yl trifluoromethanesulfonate (2.250 g, 6.89 mmol) and 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.729 g, 6.89 mmol) in dioxane (32 mL) with argon, add a solution of K2CO3 (2.86 g, 20.66 mmol) in H2O (16 mL) followed by Pd(PPh3)4 (252 mg, 0.689 mmol) and heat at 60° C. for 1 h. Cool to RT, add EtOAc, wash successively with H2O, satd. NaHCO3, then brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (1.277 g, 61%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 9.21 (d, J=0.8 Hz, 1H), 8.28 (s, 1H), 8.00 (s, 1H), 7.00 (d, J=12.4 Hz, 1H), 6.59 (d, J=9.3 Hz, 1H), 5.08 (s, 2H), 2.42 (s, 3H), 1.85 (s, 3H); MS (ESI) m/z: 302.1 (M+H+).

Provenance & Evidence