Potassium Phosphate, Tribasic → HCID 67326082, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.055 g, 0.155 mmol, prepared as in Example 2, Step 1-2), potassium phosphate (0.131 g, 0.619 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.015 g, 0.031 mmol), Pd2 dba3 (0.142 g, 0.155 mmol), and 2-(2-bromo-3-methylphenyl)-5-methyloxazole (0.078 g, 0.310 mmol). The vessel was evacuated and flushed with N2 3× before dioxane (1.00 mL) and water (0.500 mL) (each degassed by bubbling N2 gas through the solution for 10 min prior to addition) were added. The reaction mixture was stirred and heated in a microwave reactor at 130° C. for 15 min. The reaction mixture was diluted with 10:1 saturated ammonium chloride/ammonium hydroxide and extracted with EtOAc. The combined organic extracts were washed with 10:1 saturated ammonium chloride/ammonium hydroxide, water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel chromatography by eluting with 1:15:15 2M NH3 in MeOH/dichloromethane/sdiethyl ether, to provide the desired product which after triturating with diethyl ether gave 6-(2-methyl-6-(5-methyloxazol-2-yl)phenyl)-3-morpholinoquinolin-2-amine. MS (ESI, pos. ion) m/z: 401 (M+1).

Provenance & Evidence