反应详情

温度

90 °C

To a degassed mixture of N-benzyl-2-chloro-6-methoxyisonicotinamide (1.38 g, 5.00 mmol), benzophenone imine (1.0 mL, 5.78 mmol), sodium t-butoxide (1.20 g, 12.0 mmol) and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.02 g, 0.03 mmol) in toluene (40 mL) was added tris(dibenzylideneacetone)dipalladium (0.01 g, 0.01 mmol). The resulting solution was heated at 90° C. for 18 hours and concentrated in vacuo. The residue was dissolved in a mixture of tetrahydrofuran (20 mL) and 10% hydrochloric acid solution (20 mL) and stirred for 20 hours at ambient temperature. The resulting solution was neutralized with saturated sodium bicarbonate solution until pH 8-9 and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give 2-amino-N-benzyl-6-methoxyisonicotinamide (0.80 g, 62%): MS (ES+) m/z 258.5 (M+1).

1. concentrationconcentrated in vacuo
2. dissolutionThe residue was dissolved in a mixture of tetrahydrofuran (20 mL) and 10% hydrochloric acid solution (20 mL)
3. extractionextracted with ethyl acetate (3×50 mL)
4. washThe combined organic layers were washed with brine (30 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography