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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 471438Generated: October 31, 2026

Sodium Carbonate → HCID 86703878, compound

https://huagongshe.com/reaction/471438

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 2734217—
Reactant4-[(Tert-butyldimethylsilyl)oxy]-2,6-dimethylphenylboronic acidHCID 59838332—
Reactant(1S,2S)-2-[4-((R)-4-Bromo-5-cyano-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl esterHCID 86703879—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
ProductHCID 86703878HCID 8670387862.3%

Reaction Conditions

Temperature110 °C

Reaction Steps

Under nitrogen atmosphere, (1S,2S)-2-[4-((R)-4-Bromo-5-cyano-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester (Intermediate 13, 590 mg, 1.38 mmol), (4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)boronic acid (0.78 g, 2.77 mmol, WO2005/63729A1), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (54 mg, 0.138 mmol), tris(dibenzylideneacetone)dipalladium(0) (63.37 mg, 0.07 mmol) and sodium carbonate (500 mg, 4.71 mmol) are suspended in 10 mL of toluene and 5 mL of water. The reaction mixture is stirred at 110° C. for 12 h then it is concentrated under vacuum. The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 100/01 4 80/20) to give the title compound (Yield: 500 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08633182B2
Source datasetuspto-grants-2014_01
ORD IDord-0f0686db68304ac185db5084c647a974
Source noteuspto-grants-2014_01