Potassium Phosphate, Tribasic → HCID 53329357, 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(dba)3 (7.09 mg, 7.74 μmol), and 2-(2-bromo-3-methylphenyl)-4-methyloxazole (0.078 g, 0.310 mmol). The vessel was evacuated and flushed with nitrogen three times before dioxane (1.0 mL) and water (0.50 mL) (each degassed by bubbling nitrogen gas through the solution for 10 min prior to addition) were added. The reaction mixture was stirred and heated in a microwave 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 which was purified by silica gel chromatography by eluting with 1:15:15 2M NH3 in MeOH/DCM/diethyl ether to provide the desired product which after triturating with diethyl ether gave 6-(2-methyl-6-(4-methyloxazol-2-yl)phenyl)-3-morpholinoquinolin-2-amine as white solid. MS (ESI, pos. ion) m/z: 401 (M+1).

Provenance & Evidence