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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1245173Generated: October 31, 2026

Sodium Carbonate → HCID 21919148, compound

https://huagongshe.com/reaction/1245173

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantLithium ChlorideHCID 433294—
Reactant3-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 4198005—
ReactantMethyl 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoateHCID 21919123—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
ProductHCID 21919148HCID 2191914885%

Reaction Conditions

Temperature95 °C

Reaction Steps

To a solution of methyl 3-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(trifluoromethanesulfonyl)oxybenzoate (316 mg, 0.6220 mmol) in toluene (7.1 ml) were added tetrakistriphenylphosphine palladium (22 mg, 0.0190 mmol), aqueous solution of sodium carbonate (2M aqueous solution, 0.81 ml), lithium chloride (53 mg, 1.2502 mmol) and ethanolic solution (1.3 ml) of pyridine-3-boronic acid 1,3-propanediol cyclic ester (151 mg, 0.9320 mmol) and the mixture was heated with stirring at 95° C. for 16 hours. The reaction solution was diluted with ethyl acetate (100 ml), washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the title compound (231 mg, 0.5286 mmol, 85%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07122543B2
Source datasetuspto-grants-2006_10
ORD IDord-d1a8c26364814958a50cceb0c7d47497
Source noteuspto-grants-2006_10