Potassium Phosphate, Tribasic → 6-(2-(3,3-Dimethylbut-1-ynyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with a mixture of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.040 g, 0.084 mmol), Pd2(dba)3 (0.019 g, 0.021 mmol), 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.15 g, 0.422 mmol, prepared as in Example 2, Step 1-2) and potassium phosphate (0.175 mL, 2.11 mmol). The vial was evacuated and backfilled with N2. This procedure was repeated twice. Degassed dioxane (2.8 mL) and water (1.4 mL) was added. Then 2-bromo-1-(3,3-dimethylbut-1-ynyl)-3-methylbenzene (0.138 g, 0.549 mmol) was added and the reaction mixture was heated to 140° C. for 12 min in the microwave. The reaction mixture was cooled to RT and partitioned between EtOAc and water. The organic phase was washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (50-100% EtOAc/hexanes). The obtained solid was dissolved in MeOH (4 mL) and treated with 1N HCl (1 mL). The solution was eluted on an SCX cartridge with MeOH followed by 2M NH3/MeOH. The basic fraction was concentrated to afford the titled compound as a beige foam. MS (ESI, pos. ion) m/z: 400 (M+1).

Provenance & Evidence