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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1788528Generated: November 1, 2026

4-Chlorophenylboronic acid → 2-[2-[3-(4-Chlorophenyl)phenyl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

https://huagongshe.com/reaction/1788528

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Chlorophenylboronic acidHCID 74299—
ReactantSodium BicarbonateHCID 516892—
Reactant2-[2-(3-Bromophenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acidHCID 5276101—
CatalystHCID 178418397HCID 178418397—
SolventMethanolHCID 887—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
Product2-[2-[3-(4-Chlorophenyl)phenyl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acidHCID 527610242.2%

Reaction Conditions

Temperature90 °C

Reaction Steps

In dried vial with a Teflon lined screw cap, a solution of Compound 482 (156 mg, 0.31 mmol), 4-chlorophenylboronic acid (73 mg, 0.465 mmol), and Palladium Tetrakis (37 mg, 0.031 mmol) in toluene (9 mL), methanol (2 mL), and saturated sodium bicarbonate in water (900 μL) was degassed, flushed with argon, and sealed. The reaction was stirred for 16 h at 90° C. The completed reaction was then evaporated to dryness, purified via HPLC, and converted to the HCl salt using the standard procedure (as described in Compound 516) to produce the title compound (73 mg, 42% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07511145B2
Source datasetuspto-grants-2009_03
ORD IDord-8b66773aa0bf407c865d37bd2c2576a1
Source noteuspto-grants-2009_03