2-Bromoethyl methyl ether → HCID 22646598, compound

Participants

Reaction Steps

4-(4-Chloro-2-fluoroanilino)-7-methoxy-6-trifluoromethylsulphonyloxyquinoline (560 mg, 1.2 mmol), (prepared as described in Example 60), was suspended in THF (40 ml) and toluene (40 ml) and degassed several times using alternatively vacuum and argon. Tetrakis(triphenylphosphine)palladium(0) (100 mg) and sodium triisopropylsilanethiolate (600 mg, 2.8 mmol), (Tet Lett 1994, 35, 3221), were added and the mixture was heated at reflux for 3 hours. The mixture was cooled to ambient temperature and 2-bromoethyl methyl ether (1.0 g, 7.2 mmol), DMF (20 ml) and 1M tetrabutylammonium fluoride in THF (10 ml) were added. After stirring for 1 hour at ambient temperature, the mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was purified by flash chromatography eluting with ethyl acetate/isohexanes (25/75) followed by ethyl acetate/methanol (95/5). The solvent was removed by evaporation and the residue was triturated with ethyl acetate/ether (1/4), collected by filtration and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-7-methoxy-6-(2-methoxyethylthio)quinoline (210 mg, 43%).

Provenance & Evidence