4-Pyridinecarboxylicacid,5-amino-2-methyl-(9CI) synthesis

Yield:-

Steps:

Multi-step reaction with 4 steps
1: N,N-dimethyl-formamide / 15 h / 0 - 15 °C
2: potassium carbonate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / 1,4-dioxane / 13 h / 100 °C / Inert atmosphere
3: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 15 °C / 1551.49 Torr
4: sodium hydroxide; water / tetrahydrofuran / 2 h / 15 °C

References:

MERCK SHARP & DOHME CORP.;ARASAPPAN, Ashok;BUNGARD, Christopher James;FRIE, Jessica L.;HAN, Yongxin;HOYT, Scott B.;MANLEY, Peter J.;MEISSNER, Robert S.;PERKINS, James;SEBHAT, Iyassu K.;WILKENING, Robert R. WO2016/29454, 2016, A1