反应详情

温度

120 °C

In a 25 mL sealable tube under nitrogen were combined 6-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide (120 mg, 0.29 mmol) and 3-pyridinylboronic acid (53 mg, 0.43 mmol) in DME/water (3 mL: 1 mL). PdCl2(dppf)-CH2Cl2 (11.7 mg, 0.014 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. Sodium bicarbonate (72.5 mg, 0.86 mmol) was added and the insoluble mixture was heated in a microwave at 120° C. for 20 min. It was evaporated and the residue was dissolved in DCM and purified by SiO2 chromatography (eluent: gradient 100% DCM to 80:20:2 DCM/MeOH/NH4OH). Fractions were evaporated. DMF was added along with some water and the solids that precipitated were filtered, washed with water and hexanes and dried to afford the title compound (74 mg, 61%) as a light grey solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (s, 1H) 9.11 (d, J=2.02 Hz, 1H) 8.66 (t, J=4.80 Hz, 1H) 8.61 (dd, J=4.80, 1.26 Hz, 1H) 8.42 (s, 1H) 8.28 (dt, J=8.02, 1.93 Hz, 1H) 8.25 (s, 1H) 7.93 (s, 1H) 7.54 (dd, J=7.83, 4.80 Hz, 1H) 5.89 (s, 1H) 5.19 (dt, J=13.14, 6.57 Hz, 1H) 4.40 (d, J=4.80 Hz, 2H) 2.22 (s, 3H) 2.12 (s, 3H) 1.52 (s, 3H) 1.50 (s, 3H). MS(ES) [M+H]+ 416.1.

1. customIn a 25 mL sealable tube under nitrogen were combined
2. customthe resulting mixture was degassed with nitrogen for 10 min
3. customIt was evaporated
4. dissolutionthe residue was dissolved in DCM
5. custompurified by SiO2 chromatography (eluent: gradient 100% DCM to 80:20:2 DCM/MeOH/NH4OH)
6. customFractions were evaporated
7. additionDMF was added along with some water
8. customthe solids that precipitated
9. filtrationwere filtered
10. washwashed with water and hexanes
11. customdried