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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2200185Generated: October 31, 2026

Water → HCID 90020550, compound

https://huagongshe.com/reaction/2200185

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantCesium carbonateHCID 10796—
ReactantBenzophenone imineHCID 136809—
Reactant3-Bromo-5-(trifluoromethyl)pyridineHCID 11127991—
CatalystBinap, (A+-)-HCID 634876—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 90020550HCID 9002055098%

Reaction Conditions

Temperature110 °C

Reaction Steps

Add 3-bromo-5-(trifluoromethyl)pyridine (600 mg, 2.67 mmol), benzophenone imine (701 mg, 4.0 mmol), Cs2CO3 (2.17 g, 6.68 mmol), BINAP (25 mg, 0.040 mmol), Pd2(dba)3 (24 mg, 0.027 mmol) in 1,4-dioxane (10 mL), stir at 110° C. for 16 hrs. Cool to room temperature, add water (100 mL), extract with EtOAc (15 mL×3), wash the combined organic layers with brine, dry over anhydrous Na2SO4, concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=6:94) affords the target compound (850 mg, 98%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09359338B2
Source datasetuspto-grants-2016_06
ORD IDord-37b0df9789f64306950ea523754d7a57
Source noteuspto-grants-2016_06