Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2192161Generated: October 26, 2026

Ethyl Acetate → Benzenamine,4-[(6-chloro-3-methyl-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoro-

https://huagongshe.com/reaction/2192161

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantPotassium CarbonateHCID 11430—
ReactantPhenol, 4-amino-2-fluoro-HCID 2735918—
Reactantmethyl-4,6-dichloro-3-methyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylateHCID 59741007—
SolventDimethyl SulfoxideHCID 679—
ProductBenzenamine,4-[(6-chloro-3-methyl-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoro-HCID 17979286—

Reaction Conditions

Temperature120 °C

Reaction Steps

300 mg (1.16 mmol) of methyl-4,6-dichloro-3-methyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate and 320 mg (2.32 mmol) of powdered potassium carbonate are suspended in 9 ml of DMSO. The mixture is degassed, and 442 mg (3.48 mmol) of 4-amino-2-fluorophenol are added. The mixture is heated at 120° C. for 4 hours. After addition of ethyl acetate, the mixture is filtered off with suction through Celite®, and the celite is washed with ethyl acetate. The filtrate is shaken three times with saturated sodium bicarbonate solution and with saturated sodium chloride solution. The filtrate is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by column chromatography (silica gel 60, mobile phase: dichloromethane/methanol=50:1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08329716B2
Source datasetuspto-grants-2012_12
ORD IDord-1f8f2ae2bbd6410b9841019a686c8869
Source noteuspto-grants-2012_12