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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1835586Generated: October 31, 2026

Water → HCID 21943015, compound

https://huagongshe.com/reaction/1835586

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant4-Chlorophenylboronic acidHCID 74299—
ReactantSodium BicarbonateHCID 516892—
ReactantMethyl 2-[4-(2-bromo-5-nitrobenzyloxy)-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylateHCID 10210392—
CatalystHCID 178418397HCID 178418397—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductHCID 21943015HCID 2194301590.1%

Reaction Steps

Methyl 2-[4-(2-bromo-5-nitrobenzyloxy)-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate (2.0 g) obtained in Example 336, 4-chlorophenylboronic acid (590 mg) and tetrakis(triphenylphosphine)palladium (396 mg) were suspended in dimethoxyethane (40 ml), and saturated aqueous sodium hydrogencarbonate solution (20 ml) was added, which was followed by refluxing under heating for 1 hr. The reaction mixture was allowed to cool, water was added and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (n-hexane:ethyl acatate=2:1) to give the title compound (1.9 g, yield 90%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06770666B2
Source datasetuspto-grants-2004_08
ORD IDord-7f001bf40fbb44e5af9a269528557cab
Source noteuspto-grants-2004_08