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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 79525Generated: October 30, 2026

Toluene → 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(3-fluorophenyl)-1-(phenylsulfonyl)-

https://huagongshe.com/reaction/79525

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPotassium CarbonateHCID 11430—
Reactant3-Fluorophenylboronic acidHCID 2733986—
Reactant1H-Pyrrolo[2,3-B]pyridine, 5-bromo-4-chloro-1-(phenylsulfonyl)-HCID 49758885—
CatalystHCID 178418397HCID 178418397—
SolventEthanolHCID 702—
SolventWaterHCID 962—
Product1H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(3-fluorophenyl)-1-(phenylsulfonyl)-HCID 6876166373.9%

Reaction Conditions

Temperature80 °C

Reaction Steps

5-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.660 g, 1.78 mmol), 3-fluorophenylboronic acid (0.298 g, 2.13 mmol), Pd(PPh3)4 (0.103 g, 0.0888 mmol) and 10% K2CO3 (aq., 3.70 mL, 2.66 mmol) were added to an argon degassed solution of 2:1 toluene:EtOH (6 mL). The reaction was then heated to 80° C. for 18 hours. The reaction was then diluted with water and extracted with DCM. The organic fractions were dried, filtered, concentrated, and purified by column chromatography (1:1 hexanes:DCM) to give 4-chloro-5-(3-fluorophenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.508 g, 73.9% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08841304B2
Source datasetuspto-grants-2014_09
ORD IDord-9911de1f7e734dc2a130c3f4acc0a9da
Source noteuspto-grants-2014_09