反应详情

温度

50 °C

A 50-mL sealed tube was charged with Pd(OAc)2 (18 mg, 0.08 mmol) and 2,2′-bis (diphenylphosphino)-1,1′-binaphthyl (BINAP, 50 mg, 0.08 mmol) in 1,4-dioxane (10 mL). The mixture was degassed using bubbling nitrogen for 40 min and heated at 50° C. for 1 h. Then the mixture was cooled to room temperature whereupon 2-[(2,5-dichloro-4-pyridinyl)amino]-N-methyl-benzamide (300 mg, 1.01 mmol), 2-methyl-5-phenyl-2H-pyrazol-3-ylamine (704 mg, 4.06 mmol) and cesium carbonate (960 mg, 2.96 mmol) were added under an inert atmosphere. The tube was sealed and heated at 120° C. overnight. The reaction mixture was concentrated under reduced pressure and the crude product was purified by column chromatography (silica gel, eluted with dichloromethane-methanol (DCM-MeOH) 99:1 followed by purification by preparatory TLC to afford the desired compound as a off white solid (25 mg, 5%). 1H NMR (400 MHz, DMSO-d6) δ 2.76 (d, 3H, J=4.52 Hz), 3.68 (s, 3H), 6.69 (s, 1H), 6.85 (s, 1H), 7.07-7.14 (m, 1H), 7.25-7.31 (m, 1H), 7.36-7.42 (m, 2H), 7.46-7.53 (m, 1H), 7.63 (d, 1H, J=8.08 Hz), 7.69 (d, 1H, J=7.4 Hz), 7.75 (d, 2H, J=7.16 Hz), 8.04 (s, 1H), 8.69 (brs, 1H), 8.81 (s, 1H), 10.13 (s, 1H). LC-MS calculated for C23H21ClN6O (M+H) 433.15, found 433.3. HPLC purity 96% at λ=200 nm and 99% at λ=260 nm.

1. customA 50-mL sealed tube
2. customThe mixture was degassed
3. customusing bubbling nitrogen for 40 min
4. additionwere added under an inert atmosphere
5. customThe tube was sealed
6. temperatureheated at 120° C. overnight
7. concentrationThe reaction mixture was concentrated under reduced pressure
8. customthe crude product was purified by column chromatography (silica gel
9. washeluted with dichloromethane-methanol (DCM-MeOH) 99:1
10. customfollowed by purification by preparatory TLC