反应详情

温度

120 °C

To a 20 mL microwave vial was added N-(2-phenylpropan-2-yl)-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (86 mg, 0.167 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (4.8 mg, 9.99 μmol), Pd2(dba)3 (4.6 mg, 5.00 μmol), 2-bromo-6-cyclopropylpyrazine (CombiPhos Catalyst Inc., 36.5 mg, 0.183 mmol) and potassium phosphate (106 mg, 0.500 mmol) followed by purging with argon. The solids were treated with dioxane (3.0 mL) and water (0.3 mL) and heated in the microwave at 120° C. for 20 min. The mixture was treated with water and extracted with EtOAc, dried over MgSO4, filtered and concentrated. Purification (10-100% EtOAc in Hex) afforded 5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-amine (28.1 mg, 29%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 591.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.64-8.71 (2H, m), 8.39 (1H, s), 8.13 (1H, s), 8.03 (1H, d, J=8.8 Hz), 7.81 (2H, d, J=8.4 Hz), 7.78 (1H, dd, J=8.7, 1.5 Hz), 7.54 (2H, d, J=7.6 Hz), 7.35 (2H, t, J=7.7 Hz), 7.22-7.29 (3H, m), 6.01 (1H, s), 2.35 (3H, s), 2.09-2.16 (1H, m), 1.86 (6H, s), 1.20-1.24 (2H, m), 1.08-1.14 (2H, m).

1. customby purging with argon
2. additionThe solids were treated with dioxane (3.0 mL) and water (0.3 mL)
3. additionThe mixture was treated with water
4. extractionextracted with EtOAc
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification (10-100% EtOAc in Hex)