1,3-Dichloroacetone → 2-(Chloromethyl)imidazo[2,1-f][1,6]naphthyridine

To a solution of 1,6-naphthyridin-5-amine (145 mg, 1 mmol) in 1,2-dimethoxyethane (5 mL) was added 1,3-dichloropropan-2-one (140 mg, 1.1 mmol). The solid dissolved immediately and a white precipitate was observed. The mixture was stirred at room temperature for 1 h, and then was cooled to 0° C. for 20 min. The resulting mixture was filtered to give a white solid. The precipitate was suspended in EtOH (40 mL) and heated at reflux. After refluxing for 2 h, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in water and saturated aqueous NaHCO3 solution was added to adjust the pH value to 7. A white suspension formed during the course of addition. The resulting mixture was stirred for 20 min and then filtered to give 2-(chloromethyl)imidazo[2,1-f][1,6]naphthyridine as a white solid (130 mg). MS (ESI): m/z 218 [M+H]+.

1. dissolutionThe solid dissolved immediately
2. temperaturewas cooled to 0° C. for 20 min
3. filtrationThe resulting mixture was filtered
4. customto give a white solid
5. temperatureheated
6. temperatureat reflux
7. temperatureAfter refluxing for 2 h
8. concentrationthe reaction mixture was concentrated under reduced pressure
9. dissolutionThe residue was dissolved in water
10. additionsaturated aqueous NaHCO3 solution was added
11. customA white suspension formed during the course of addition
12. stirringThe resulting mixture was stirred for 20 min
13. filtrationfiltered

ORD record

ord-174a557d7fd741c3903308ee1b89d4d8

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969349B2