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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 576290Generated: October 26, 2026

Potassium Phosphate, Tribasic → ethyl 3-(3-(naphthalen-1-yloxy)propyl)-7-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-indole-2-carboxylate

https://huagongshe.com/reaction/576290

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium Phosphate, TribasicHCID 62657—
Reactant1,3,5-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 2795311—
Reactant2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11269872—
Reactantethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylateHCID 68938945—
Catalystpalladium(II) acetateHCID 167845—
SolventTolueneHCID 1140—
Productethyl 3-(3-(naphthalen-1-yloxy)propyl)-7-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1H-indole-2-carboxylateHCID 68933185—

Reaction Conditions

Temperature110 °C

Reaction Steps

To a mixture of ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate (EXAMPLE 1C) (1.605 g) and 1,3,5-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.838 g) in toluene (25 ml) was added diacetoxypalladium (0.080 g), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.291 g), and K3PO4 (2.259 g). The resulting mixture was stirred at 110° C. overnight. Silica gel (25 g) was added and the mixture was carefully dried on house vacumn overnight. The gel powder was loaded onto a flash column and eluted with 0-50% ethyl acetate in dichloromethane to provide the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09035047B2
Source datasetuspto-grants-2015_05
ORD IDord-20c57659340e42dfa224f71a6da16b30
Source noteuspto-grants-2015_05