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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1485937Generated: October 31, 2026

Potassium Fluoride → 4-chloro-3-(4,6-dichloro-pyridin-3-yl)-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl benzamide

https://huagongshe.com/reaction/1485937

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium FluorideHCID 522689—
Reactant(4,6-Dichloropyridin-3-yl)boronic acidHCID 45789871—
Reactant3-bromo-4-chloro-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl-benzamideHCID 68603607—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,4-DioxaneHCID 31275—
Product4-chloro-3-(4,6-dichloro-pyridin-3-yl)-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl benzamideHCID 59370329—

Reaction Conditions

Temperature110 °C

Reaction Steps

A mixture of dioxane (1.0 mL) containing 3-bromo-4-chloro-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl-benzamide (44.0 mg, 0.11 mmol), Pd2(dba)3 (10 mg, 0.01 mmol), P(t-Bu)3HBF4 (7 mg, 0.022 mmol), KF (22 mg, 0.38 mmol) and 2,4 dichloropyridine-5-boronic acid (21 mg, 0.11 mmol) was degassed by bubbling N2 for 5 minutes and then sealed and heated at 110° C. overnight. The mixture was filtered and purified by preparative LCMS to yield 4-chloro-3-(4,6-dichloro-pyridin-3-yl)-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl benzamide 7-1. MS [M+H]+: 478.0; tR=5.26 min. (method 2)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09422310B2
Source datasetuspto-grants-2016_08
ORD IDord-d216a60d92a448ddb30ceac2635fb7f0
Source noteuspto-grants-2016_08