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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1878636Generated: October 30, 2026

Aniline → 1-[(4-methylphenyl)sulphonyl]-N-phenyl-1H-pyrrolo[2,3-b]pyridin-5-amine

https://huagongshe.com/reaction/1878636

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAnilineHCID 6115—
ReactantCesium carbonateHCID 10796—
Reactant1H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-HCID 22477353—
Catalyst1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
SolventTolueneHCID 1140—
Product1-[(4-methylphenyl)sulphonyl]-N-phenyl-1H-pyrrolo[2,3-b]pyridin-5-amineHCID 67131718172.7%

Reaction Steps

Put 750 mg of 5-bromo-1-[(4-methylphenyl)sulphonyl]-1H-pyrrolo[2,3-b]pyridine in 19 cm3 of toluene, 54 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 970 mg of caesium carbonate, 280 mg of aniline and 40 mg of tri(dibenzylideneacetone)dipalladium(0) in a microwave oven reactor. Irradiate the reactor in a microwave oven for forty-five minutes at 150° C. After cooling, filter the reaction mixture, then reduce to dryness under vacuum in a rotary evaporator. Combine the brown residue with another two residues obtained similarly, then purify by flash chromatography on a silica column with dichloromethane eluent to give 1.34 g of 1-[(4-methylphenyl)sulphonyl]-N-phenyl-1H-pyrrolo[2,3-b]pyridin-5-amine in the form of a beige powder with the following physical characteristics:

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08314121B2
Source datasetuspto-grants-2012_11
ORD IDord-a4ec31543336465fb57592e270d4f6f3
Source noteuspto-grants-2012_11