Acetic Acid → Ethyl 3-(5-(3-chloro-2-(((4'-chloro-2-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

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Reaction Steps

Solid NaBH(OAc)3 (2.6 g, 12.1 mmol) was added to a DCE solution (16 mL) of ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate (2.6 g, 6.1 mmol) and 4′-chloro-2-methyl-[1,1′-biphenyl]-4-amine (1.6 g, 7.3 mmol), and AcOH (1.4 mL, 1.2 mmol) and the resulting mixture was stirred at room temperature. After 2 h additional NaBH(OAc)3 (2.6 g, 12.1 mmol) was added. After 4 h the resulting mixture was diluted with EtOAc and 2M aqueous K2CO3 and the layers were separated. The aqueous phase was added was extracted with EtOAc and the combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Provenance & Evidence