Morpholine → 4,8-Dichloro-2-(2-isopropyl-thiazol-4-yl)-7-(2-morpholin-4-yl-ethoxy)-quinoline

Participants

Reaction Steps

4,8-Dichloro-7-(2,2-dimethoxy-ethoxy)-2-(2-isopropyl-thiazol-4-yl)-quinoline (250 mg, 0.565 mmol) was dissolved in AcOH (5.0 mL) and 2N HCl(aq). The reaction mixture was placed in a 60° C. oil bath and stirred for 1 h. Remove solvent under reduced pressure. The crude material was taken up in EtOAc and washed with ½ sat NaHCO3(aq). Organics were dried over Na2SO4, filtered and was concentrated. The crude material was then taken up in CH2Cl2. Morpholine (77 μL, 0.88 mmol) was added to the reaction mixture and stirred for 15 min. NaBH(OAc)3 (161 mg, 0.761 mmol) and AcOH (1 drop) were added and the reaction was monitored by LC/MS. After 5 min the reaction was determined to be complete. The mixture was diluted with DCM and washed with ½ sat brine, dried with Na2SO4, filtered and was concentrated. 4,8-dichloro-2-(2-isopropyl-thiazol-4-yl)-7-(2-morpholin-4-yl-ethoxy)-quinoline (218 mg, 86%) was isolated by silica gel chromatography as a yellow solid.

Provenance & Evidence