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

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	4-Aminobiphenyl	HCID 7102	—
Reactant	Sodium triacetoxyborohydride	HCID 5049666	—
Reactant	Ethyl 3-(5-(2-formylphenyl)picolinamido)propanoate	HCID 86674243	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Ethyl 3-(5-(2-(([1,1'-biphenyl]-4-ylamino)methyl)phenyl)picolinamido)propanoate	HCID 71059913	—

Reaction Conditions

Temperature	40 °C

Reaction Steps

Solid NaBH(OAc)3 (214 mg, 1.0 mmol) was added to a THF solution of ethyl 3-(5-(2-formylphenyl)picolinamido)propanoate (220 mg, 0.7 mmol), [1,1′-biphenyl]-4-amine (171 mg, 1.0 mmol), and AcOH (0.04 mL, 0.7 mmol) and the resulting mixture was warmed to 40° C. After 18 h the resulting mixture diluted with EtOAc washed with water and brine, dried (Na2SO4), dry-packed onto silica gel and purified via column chromatography to yield the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748624B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-8686137dd79b40e58b8f85e46187543f
Source note	uspto-grants-2014_06