反应详情

温度

140 °C

A mixture of 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.099 g, 0.279 mmol), (2-bromo-3-methylphenyl)(tetrahydrofuran-2-yl)methanone (0.050 g, 0.186 mmol), potassium phosphate tribasic (0.077 mL, 0.929 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.018 g, 0.037 mmol), and Pd2(dba)3 (8.51 mg, 9.29 μmol) were treated with dioxane (1.2 mL) and water (0.62 mL) in a medium-sized Smith synthesizer vial. The mixture was heated to 140° C. for 12 min in a microwave reactor. The reaction mixture was filtered then partitioned between EtOAc and water, organics were washed with water and brine and then concentrated in vacuo. The crude product was purified by silica flash chromatography (1-10% MeOH/DCM) and then by HPLC (10-75% acetonitril/H2O; TFA modifier). A single fraction was treated with NH4OH, concentrated, filtered and air-dried to afford (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(tetrahydrofuran-2-yl)methanone. MS (ESI, pos. ion) m/z: 418 (M+1).

1. filtrationThe reaction mixture was filtered
2. customthen partitioned between EtOAc and water
3. washorganics were washed with water and brine
4. concentrationconcentrated in vacuo
5. customThe crude product was purified by silica flash chromatography (1-10% MeOH/DCM)
6. additionA single fraction was treated with NH4OH
7. concentrationconcentrated
8. filtrationfiltered
9. customair-dried