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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1641293Generated: November 3, 2026

Ethyl Acetate → 3-fluoro-N-(4-hex-1-enyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamide

https://huagongshe.com/reaction/1641293

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantCesium carbonateHCID 10796—
ReactantHex-1-enylboronic AcidHCID 2773444—
ReactantN-(4-bromo-naphthalen-1-yl)-3-fluoro-5-morpholin-4-yl-benzamideHCID 59553247—
Solvent1,4-DioxaneHCID 31275—
Product3-fluoro-N-(4-hex-1-enyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamideHCID 66737973107.6%

Reaction Steps

N-(4-Bromo-naphthalen-1-yl)-3-fluoro-5-morpholin-4-yl-benzamide (2.5 g, 5.8 mmol), 1-hexenyl boronic acid (1.06 g, 8.3 mmol), cesium carbonate (3.04 g, 9.34 mmol) and tetrakis triphenylphosphine palladium(0) (100 mg) in dioxane (22 ml) are heated to 100° C. under nitrogen for 24 hours. The mixture is then poured into ethyl acetate (200 ml) and washed with water (2×100 ml). The organic layer is dried over anhydrous sodium sulfate and evaporated to dryness to give 3-fluoro-N-(4-hex-1-enyl-naphthalen-1-yl)-5-morpholin-4-yl-benzamide as a brown solid (2.7 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08114873B2
Source datasetuspto-grants-2012_02
ORD IDord-3ea703e6797d433992fb0c6db4946f77
Source noteuspto-grants-2012_02