Tetrahydro-4H-pyran-4-one → 4-(6-bromo-2-(4-methoxybenzylamino)quinolin-3-yl)tetrahydro-2H-pyran-4-ol

Participants

Reaction Conditions

Reaction Steps

Isopropylmagnesium chloride, 2M THF (1.322 mL, 2.64 mmol) was added to a solution of 6-bromo-3-iodo-N-(4-methoxybenzyl)quinolin-2-amine (1.24 g, 2.64 mmol) in THF (25 mL) cooled to −20° C. After stirring for 5 min, an additional amount of iso-propylmagnesium chloride, 2M THF (1.322 mL, 2.64 mmol) was added and the solution was stirred 10 min at this temperature. Next, dihydro-2H-pyran-4(3H)-one (0.293 mL, 3.17 mmol) was added and the reaction was allowed to come to 0° C. After 20 min, the reaction mixture was diluted with saturated ammonium chloride and extracted with EtOAc. The combined organic extracts were washed with saturated ammonium chloride, water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material which was purified by silica gel chromatography by eluting with 1:3 to 1:1 EtOAc in hexane, to provide 4-(6-bromo-2-(4-methoxybenzylamino)quinolin-3-yl)tetrahydro-2H-pyran-4-ol as light-yellow oil.

Provenance & Evidence