Hydrochloric Acid → 3-(5-amino-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

関与物質

反応条件

反応手順

To a solution of 3-(5-amino-2-methylphenyl)-7-chloro-1-methyl-1,6-naphthyridin-2-one 8 (0.53 mmol) in dioxane (3 mL) was added triphenylphosphine (0.08 mmol), Pd2(dba)3 (16 umol) and trimethylaluminum (0.8 mL of a 2.0 M solution in toluene). The mixture was degassed for 10 minutes. The reaction vial was sealed and heated via microwave for 10 minutes at 150° C. The reaction was cooled to rt and poured into 1M HCl (30 mL) and washed with EtOAc. The aqueous layer was made basic with 3M NaOH and extracted with EtOAc (3×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and reduced to dryness by evaporation. The crude yellow oil was purified by flash chromatography on silica with DCM containing 3-5% MeOH as eluant to yield a yellow glassy solid 15. 1H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 7.63 (s, 1H), 7.08 (s, 1H), 7.05 (d, J=8.4 Hz, 1H), 6.65 (dd, J=8.4, 2.4 Hz, 1H), 6.57 (d, J=2.4 Hz, 1H), 3.72 (s, 3H), 2.70 (s, 3H), 2.11 (s, 3H). MS m/z (M+1)+: 280.1.

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