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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1773318Generated: November 1, 2026

Cesium carbonate → HCID 118699712, compound

https://huagongshe.com/reaction/1773318

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantMethyl 3-bromobenzoateHCID 12070—
ReactantBinap, (A+-)-HCID 634876—
ReactantHCID 118699713HCID 118699713—
Catalystpalladium(II) acetateHCID 167845—
SolventTolueneHCID 1140—
ProductHCID 118699712HCID 11869971269%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 6,7,8,9-Tetrahydrothieno[3,2-c]-2,7-naphthyridine (3.0 g, 15.77 mmol, prepared as previously described), methyl-3-bromobenzoate (3.90 g, 18.14 mmol), palladium(II)acetate (354 mg, 1.577 mmol), racemic BINAP (982 mg, 1.577 mmol) and cesium carbonate (7.19 g, 22.08 mmol) in toluene (270 ml) was heated at 100° C. with stirring for 18 hours. Upon cooling to room temperature, the insolubles were filtered off (celite) and washed with EtOAc. The washing was combined with the filtrate and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, EtOAc) gave the product as a yellow glass (3.54 g, 69%). MS (APCl): (M+1)+=325;

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09255096B1
Source datasetuspto-grants-2016_02
ORD IDord-1aaaef26583f4ea6b9fcb5f9abee7d42
Source noteuspto-grants-2016_02