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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 646139Generated: October 30, 2026

Ethanol → 3-Chloro-1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyridin-2-yl)indole-2-carboxylic acid ethyl ester

https://huagongshe.com/reaction/646139

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantSodium CarbonateHCID 10340—
Reactant2-Bromo-5-(trifluoromethyl)pyridineHCID 2736434—
Reactant3-Chloro-5-(dihydroxyboryl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl esterHCID 68697845—
CatalystHCID 178418397HCID 178418397—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
Product3-Chloro-1-(4-isopropoxyphenyl)-5-(5-trifluoromethylpyridin-2-yl)indole-2-carboxylic acid ethyl esterHCID 6847510395%

Reaction Conditions

Temperature85 °C

Reaction Steps

A stirred mixture of 3-chloro-5-(dihydroxyboryl)-1-(4-isopropoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester (200 mg, 0.50 mmol; see step (b) above), 2-bromo-5-(trifluoromethyl)pyridine (170 mg, 0.75 mmol), sodium carbonate (2M in water, 0.75 mL, 1.5 mmol), Pd(PPh3)4 (29 mg, 0.025 mmol), EtOH (0.4 mL) and toluene (1.6 mL) was heated at 85° C. for 3 h. The reaction was diluted with EtOAc, washed with brine, dried over MgSO4, concentrated and purified by chromatography to give the sub-title compound (239 mg, 95%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07705023B2
Source datasetuspto-grants-2010_04
ORD IDord-a071cee0c7ec45bdbee703abaa00052f
Source noteuspto-grants-2010_04