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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 16421Generated: October 24, 2026

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

https://huagongshe.com/en/reaction/16421

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantPotassium CarbonateHCID 11430—
ReactantPhenol, 4-amino-2-fluoro-HCID 2735918—
Reactant1-acetyl-4,6-dichloro-3-methyl-1H-pyrrolo[2,3-b]pyridineHCID 17979289—
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 1-acetyl-4,6-dichloro-3-methyl-1H-pyrrolo[2,3-b]pyridine (from example XL) 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 (diatomaceous earth) and the filtercake is washed with ethyl acetate. The filtrate is extracted three times with sat. sodium bicarbonate solution and with sat. 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: DCM:methanol=50:1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07737153B2
Source datasetuspto-grants-2010_06
ORD IDord-f54b7a1f971e4a7496946caf6e8bee25
Source noteuspto-grants-2010_06