Table 1.
Suzuki–Miyaura coupling conditions for JH-VII-139-1. Reaction conditions: all reactions were carried out using triflate 10 (1.2 equiv), boronic acid 13 (1 equiv), Pd(dppf)Cl2 as catalyst (5%) and tBuXPhos (10%).
| Temp. (°C) |
Solvent | Base | Time (h) | Ratio (%) * 10 |
Ratio (%) * 14: 9: JH-VII-139-1 |
Isolated Yield for JH-VII-139-1 (%) |
|---|---|---|---|---|---|---|
| 85 | DME/H2O | K2CO3 | 24 | 0 | 40: 57: 3 | ND |
| 120 | DME/H2O | Cs2CO3 | 24 | 0 | 12: 80: 8 | ND |
| 120 (MW) | dioxane | K2CO3 | 2 | 96 | 0: 4: 0 | 0 |
| 140 (MW) | dioxane | K2CO3 | 1 | 90 | 0: 10: 0 | 0 |
| 85 | DME/H2O | K2CO3 | 24 | 0 | 22: 64: 14 | 8 |
| 85 (MW) | dioxane/H2O | K2CO3 | 2 | 0 | 0: 45: 55 | 50 |
| 100 (MW) | dioxane/H2O | K2CO3 | 2 | 0 | 0: 82: 18 | 17 |
| 60 (MW) | dioxane/H2O | K2CO3 | 6 | 30 | 0: 4: 66 | 59 |
| 70 (MW) | dioxane/H2O | K2CO3 | 2 | 0 | 0: 12: 88 | 80 |
* Ratio % of JH-VII-139-1 to 9, 14 as determined by integration of the corresponding peaks in the LCMS chromatogram (254 nm). ND = not determined, MW = microwave irradiation.