反应详情

温度

70 °C

Argon was bubbled through a suspension of 4-(4-bromo-thiazolo[5,4-c]pyridine-2-yl)-3,5-dichloro-benzonitrile (92 mg, 0.24 mmol), 2-amino-isonicotinonitrile (26 mg, 0.22 mmol), XantPhos (14 mg, 0.024 mmol) and cesium carbonate (195 mg, 0.6 mmol) in dioxane (2.5 ml) for 5 minutes then Pd2(dba)3 (11 mg, 0.012 mmol) was added. The reaction was heated at 70° C. for 8 hours and then cooled to room temperature. The reaction was partitioned between water (10 mL) and DCM (20 mL). The organic layer was separated, dried over Na2SO4 and concentrated to dryness under reduced pressure. The resultant residue was purified by silica gel flash chromatography eluting with 0-60% EtOAc in DCM. The resultant solid was triturated with diethyl ether, filtered, and left to air dry to give the desired compound as a yellow solid (64 mg, 63% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.74 (br s, 1H), 8.50 (dd, J=5.1, 0.9 Hz, 1H), 8.44 (d, J=5.6 Hz, 1H), 8.39 (s, 2H), 8.23 (s, 1H), 7.79 (d, J=5.6 Hz, 1H), 7.38 (dd, J=5.1, 1.4 Hz, 1H). LCMS (Method C): RT=4.70 min, m/z: 423 [M+H+].

1. temperaturecooled to room temperature
2. customThe reaction was partitioned between water (10 mL) and DCM (20 mL)
3. customThe organic layer was separated
4. dry with materialdried over Na2SO4
5. concentrationconcentrated to dryness under reduced pressure
6. customThe resultant residue was purified by silica gel flash chromatography
7. washeluting with 0-60% EtOAc in DCM
8. customThe resultant solid was triturated with diethyl ether
9. filtrationfiltered
10. waitleft to air
11. customdry