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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 405169Generated: October 30, 2026

Acetic Acid → Methyl 5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinate

https://huagongshe.com/reaction/405169

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactant4-Bromo-3-fluoroanilineHCID 821848—
ReactantSodium triacetoxyborohydrideHCID 5049666—
ReactantHCID 86674254HCID 86674254—
Solvent1,2-DichloroethaneHCID 11—
SolventEthyl AcetateHCID 8857—
ProductMethyl 5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinateHCID 71060114—

Reaction Steps

Solid NaBH(OAc)3 (491 mg, 2.3 mmol) was added to a DCE solution (4 mL) of methyl 5-(5-fluoro-2-formylphenyl)picolinate (300 mg, 1.2 mmol), 4-bromo-3-fluoroaniline (242 mg, 1.3 mmol), and AcOH (0.27 mL, 4.6 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with EtOAc washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08748624B2
Source datasetuspto-grants-2014_06
ORD IDord-8962f3de38a84cb48e0ff9f948ad15f3
Source noteuspto-grants-2014_06