反应详情

A mixture of 4-((4-(benzyloxy)benzyl)(4H-1,2,4-triazol-4-yl)amino)-2-bromobenzonitrile (CAB05114, 0.460 g, 1.0 mmol), 4-cyanophenylboronic acid (0.184 g, 1.25 mmol), dimethoxyethane (20 mL) and 2M Na2CO3 (20 mL) was heated to reflux before Pd2(dba)3 (0.05 g) was added and heating was continued for 5 hours. After cooling to room temperature EtOAc (50 mL) was added to and the mixture was filtered (celite). The organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography [SiO2, CHCl3/acetone (2:1)] to afford CAB06075 (4.03 g, 71%) as a white solid. Mp. 234-237-113° C.; 1H NMR (400 MHz, DMSO-d6) δ 5.02 (s, 4H), 6.72 (dd, J=8.6, 2.7 Hz, 1H), 6.91 (d, J=2.7 Hz, 1H), 6.95 (AA′BB′, 2H), 7.21 (AA′BB′, 2H), 7.30-7.45 (m, 5H), 7.75 (AA′BB′, 2H), 7.90 (d, J=8.6 Hz, 1H), 8.02 (AA′BB′, 2H), 8.75 (s, 2H); 13C NMR (100.6 MHz, DMSO-d6) δ 56.5, 69.2, 101.7, 111.7, 113.4, 113.7, 114.1, 114.8, 118.3, 118.4, 126.4, 127.8, 127.9, 128.4, 129.7, 130.0, 130.1, 132.7, 135.6, 136.9, 142.3, 143.3, 144.5, 145.9, 151.5, 158.2; LRMS (ES+): m/z 4833 (100%, [M+H]+); HRMS (ES+) calcd for C30H23N6O [M+H]+: 483.1928. found 483.1918.

1. temperaturewas heated
2. additionwas added
3. temperatureheating
4. additionwas added to and the mixture
5. filtrationwas filtered (celite)
6. customThe organic layer was separated
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash chromatography [SiO2, CHCl3/acetone (2:1)]
10. customto afford CAB06075 (4.03 g, 71%) as a white solid
11. custom237-113° C.