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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2408441Generated: October 30, 2026

Sodium Sulfate → (E)-3-{1-[4-(1-methyl-1H-indol-5-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide

https://huagongshe.com/reaction/2408441

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium SulfateHCID 24436—
Reactant1-Methyl-1H-indole-5-boronic acidHCID 2759867—
Reactant(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamideHCID 86621691—
CatalystDichlorobis(triphenylphosphine)palladiumHCID 6102075—
Solvent1,2-DimethoxyethaneHCID 8071—
Product(E)-3-{1-[4-(1-methyl-1H-indol-5-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamideHCID 86621684—

Reaction Steps

A mixture of 0.4 g (E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide, 0.231 g N-Methylindol-5-boronic acid and 14 ml dimethoxyethane is slightly heated and to this mixture are added bis(triphenylphosphine)palladium(II)chloride and 1.5 ml of a 2M aqueous sodium sulfate solution. This mixture is heated to reflux temperature under an inert gas atmosphere overnight. After cooling the mixture is filtered, evaporated and the residue is partitioned between ethyl acetate and a 5% aqueous solution of sodium bicarbonate. The organic phase is dried and evaporated and the residue is purified by silica gel flash chromatography.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08815855B2
Source datasetuspto-grants-2014_08
ORD IDord-376ee4baf3c74b70bfbc6d38e36617f4
Source noteuspto-grants-2014_08