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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 454123Generated: October 26, 2026

Potassium Carbonate → 4-(indol-5-yloxy)-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline

https://huagongshe.com/reaction/454123

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant5-HydroxyindoleHCID 16054—
Reactant4-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazolineHCID 22030690—
SolventDimethylformamideHCID 6228—
Product4-(indol-5-yloxy)-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazolineHCID 2203091817%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 4-chloro-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline (360 mg, 1.00 mmol), potassium carbonate (215 mg, 1.56 mmol) and 5-hydroxyindole (147 mg, 1.10 mmol) in DMF (8.0 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient temperature. The solvent was removed by evaporation and the residue purified by silica column chromatography eluting with methanol (2.5 to 5%) in dichloromethane. The resulting solid was recrystallised from ethyl acetate, filtered and washed with diethyl ether to give 4-(indol-5-yloxy)-6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazoline (77 mg, 17%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08492560B2
Source datasetuspto-grants-2013_07
ORD IDord-837b0946abb146ec898c168d0cf07166
Source noteuspto-grants-2013_07