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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2197017Generated: October 29, 2026

1,2-Dimethoxyethane → HCID 66974699, compound

https://huagongshe.com/reaction/2197017

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DimethoxyethaneHCID 8071—
ReactantSodium BicarbonateHCID 516892—
Reactant4-Methylpyridine-3-Boronic AcidHCID 2762711—
Reactanttert-Butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamateHCID 57522258—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
ProductHCID 66974699HCID 6697469952%

Reaction Conditions

Temperature80 °C

Reaction Steps

tert-Butyl{[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (431 mg), (4-methylpyridin-3-yl)boronic acid (206 mg), sodium hydrogencarbonate (253 mg) and tetrakis(triphenylphosphine)palladium (87 mg) were added to a degassed mixture of 1,2-dimethoxyethane (8 mL) and water (2 mL), and the mixture was stirred under a nitrogen atmosphere at 80° C. for 6 hr. The reaction mixture was allowed to cool, a saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→0:1) to give the title compound as a colorless oil (yield 230 mg, 52%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08338461B2
Source datasetuspto-grants-2012_12
ORD IDord-dd1fad89b35d4c91957bb0fcc79cfd46
Source noteuspto-grants-2012_12