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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 873534Generated: October 30, 2026

Water → HCID 117700856, compound

https://huagongshe.com/reaction/873534

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium CarbonateHCID 10340—
ReactantHCID 117700521HCID 117700521—
Reactant[4-Methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]boronic acidHCID 131732562—
SolventEthyl AcetateHCID 8857—
SolventWater 1,2-dimethoxyethaneHCID 18180031—
ProductHCID 117700856HCID 11770085644%

Reaction Conditions

Temperature80 °C

Reaction Steps

Sodium carbonate (238 mg, 2.24 mmol) and tetrakistriphenylphosphine palladium(0) (86.3 mg, 74.7μμmol) were added to a solution of the methyl 1-(6-bromopyridin-2-yl)-D-prolinate (213 mg, 747 μmol) obtained in Example 15-1 and the [4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]boronic acid (317 mg, 747 μmol) obtained in Example 1-1 in dimethoxyethane/water (3:1, v/v) (4 mL) at room temperature. The mixture thus obtained was stirred at 80° C. for 4 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate three times. The organic layer thus obtained was dried over anhydrous magnesium sulfate, and the solvent was then distilled away under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=8:2 to 1:3, v/v) to obtain the title compound (190 mg, yield: 44%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08975263B2
Source datasetuspto-grants-2015_03
ORD IDord-a9832719f4c6439ea89bdadd58fb6962
Source noteuspto-grants-2015_03