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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2199829Generated: October 29, 2026

Cesium carbonate → (E)-6-methoxy-5-(4-methylpiperazin-1-yl)-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H inden-1-one

https://huagongshe.com/reaction/2199829

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant1-MethylpiperazineHCID 53167—
ReactantBinap, (A+-)-HCID 634876—
Reactant(E)-5-bromo-6-methoxy-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-oneHCID 117940380—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
Product(E)-6-methoxy-5-(4-methylpiperazin-1-yl)-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H inden-1-oneHCID 117940096—

Reaction Conditions

Temperature110 °C

Reaction Steps

To a solution of 152 (120 mg, 0.3009 mmol) and 4-methylpiperazine (60.1 mg, 0.6105 mmol) in toluene was added cesium carbonate (197.2 mg, 0.6015 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd2(dba)3 (13.7 mg, 0.0150 mmol) and BINAP (28.0 mg, 0.0451 mmol) was added and again degassed and purged with nitrogen for another 10 min. The reaction was heated to 110° C. overnight under sealed conditions. The reaction was diluted with chloroform and filtered through celite Bed. The organic layer was concentrated to get the crude compound 155 which was purified through flash chromatography by using 100-200 mesh silica gel eluting the compound at 25% ethyl acetate in hexane as pale yellow coloured solid (E)-6-methoxy-5-(4-methylpiperazin-1-yl)-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H inden-1-one 155.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09359315B2
Source datasetuspto-grants-2016_06
ORD IDord-d739fbd41d4741cd9d86b08d4b5a589d
Source noteuspto-grants-2016_06