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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1645287Generated: October 26, 2026

Cesium carbonate → 5-Chloro-3-((5-(6-(2-morpholinoethylamino)pyridin-3-yl)furan-2-yl)methylene)indolin-2-one

https://huagongshe.com/reaction/1645287

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantN-(2-Morpholinoethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 17750274—
Reactant3-((5-Bromofuran-2-yl)methylene)-5-chloroindolin-2-oneHCID 66772829—
Solvent1,4-Dioxane--water (1/1)HCID 21886435—
Product5-Chloro-3-((5-(6-(2-morpholinoethylamino)pyridin-3-yl)furan-2-yl)methylene)indolin-2-oneHCID 66772494—

Reaction Conditions

Temperature120 °C

Reaction Steps

To 3-((5-bromofuran-2-yl)methylene)-5-chloroindolin-2-one (50 mg, 0.155 mmol) in dioxane/water (5% water) was added Cs2CO3 (152 mg, 0.466 mmol) and N-(2-morpholinoethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (62 mg, 0.186 mmol). The mixture was degassed with nitrogen for 5 minutes then heated in microwave for 20 minutes at 120° C. The solution was diluted with water and the solid formed was isolated by filtration. The solid was purified by HPLC to yield 5-chloro-3-((5-(6-(2-morpholinoethylamino)pyridin-3-yl)furan-2-yl)methylene)indolin-2-one. LCMS (M+1=451).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08124649B2
Source datasetuspto-grants-2012_02
ORD IDord-c1979d71213c4dc2b0debd7bb225ccd6
Source noteuspto-grants-2012_02