Potassium Phosphate, Tribasic → (2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanone

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Reaction Conditions

Reaction Steps

(2-Bromophenyl)(tetrahydro-2H-pyran-4-yl)methanone (0.46 g, 1.69 mmol), 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.50 g, 1.13 mmol, prepared as in Example 2, Step 1-2), potassium phosphate tribasic (0.37 mL, 4.50 mmol), 2-dicyclohexylphosphino-2′,4′,6′,-triisopropylbiphenyl (0.054 g, 0.113 mmol), and tris(dibenzylideneacetone)dipalladium (0) chloroform adduct (0.029 g, 0.028 mmol) were suspended in a mixture of dioxane (3 mL) and water (0.5 mL) and heated in the microwave to 120° C. for 30 min. The crude material was partitioned between water (100 mL) and ethyl acetate (200 mL). The organic layer was separated, dried with magnesium sulfate and evaporated to dryness under reduced pressure before purification using silica column chromatography (0-5% MeOH in DCM). The isolated material was further purified using silica column chromatography (60-100% ethyl acetate in hexane) to give (2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanone. MS (ESI, pos. ion) m/z: 418 (M+1).

Provenance & Evidence