| 96% |
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; Cs2CO3 In 1,4-dioxane; lithium hydroxide monohydrate at 120℃; for 18h; Inert atmosphere; |
13.1 Step 1: Preparation of 6-(4-fluorophenyl)-cinnolin-4-ol
Nitrogen was bubbled for 10 minutes through a suspension of 6-bromo-cinnolin-4- ol (500 mg, 2.22 mmol), 4-fluorophenyl boronic acid (466 mg, 3.33 mmol), pd(dppf)Cl2 (91 mg, 0.11 mmol) in 1,4-dioxane (10 mL). A solution of cesium carbonate (1448 mg, 4.44 mmol) in water (3 mL) was added and the mixture was stirred at 120 °C for 18 hours. The reaction mixture was cooled to RT, water (10 mL) was added and the resulting solid was collected by filtration, washed with 9:1 Et2O / MeOH (3 × 10 mL) and air dried to give the title compound as a brown solid (514 mg, 96%). H NMR (400 MHz, DMSO): δ 8.22 (d, J = 2.0 Hz, 1 H), 7.91-7.89 (m, 2 H), 7.81- 7.73 (m, 3 H), 7.32 (dd, J = 8.8, 8.8 Hz, 2 H). OH not observed. |
| 96% |
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; Cs2CO3 In 1,4-dioxane; lithium hydroxide monohydrate at 120℃; for 18h; Inert atmosphere; |
13.1 Step 1: Preparation of 6-(4-fluorophenyl)-cinnolin-4-ol
Nitrogen was bubbled for 10 minutes through a suspension of 6-bromo-cinnolin-4- ol (500 mg, 2.22 mmol), 4-fluorophenyl boronic acid (466 mg, 3.33 mmol), pd(dppf)Cl2 (91 mg, 0.11 mmol) in 1,4-dioxane (10 mL). A solution of cesium carbonate (1448 mg, 4.44 mmol) in water (3 mL) was added and the mixture was stirred at 120 °C for 18 hours. The reaction mixture was cooled to RT, water (10 mL) was added and the resulting solid was collected by filtration, washed with 9:1 Et2O / MeOH (3 × 10 mL) and air dried to give the title compound as a brown solid (514 mg, 96%). H NMR (400 MHz, DMSO): δ 8.22 (d, J = 2.0 Hz, 1 H), 7.91-7.89 (m, 2 H), 7.81- 7.73 (m, 3 H), 7.32 (dd, J = 8.8, 8.8 Hz, 2 H). OH not observed. |
| 96% |
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; Cs2CO3 In 1,4-dioxane; lithium hydroxide monohydrate at 120℃; for 18h; Inert atmosphere; |
13.1 Step 1: Preparation of 6-(4-fluorophenyl)-cinnolin-4-ol
Nitrogen was bubbled for 10 minutes through a suspension of 6-bromo-cinnolin-4- ol (500 mg, 2.22 mmol), 4-fluorophenyl boronic acid (466 mg, 3.33 mmol), pd(dppf)Cl2 (91 mg, 0.11 mmol) in 1,4-dioxane (10 mL). A solution of cesium carbonate (1448 mg, 4.44 mmol) in water (3 mL) was added and the mixture was stirred at 120 °C for 18 hours. The reaction mixture was cooled to RT, water (10 mL) was added and the resulting solid was collected by filtration, washed with 9:1 Et2O / MeOH (3 × 10 mL) and air dried to give the title compound as a brown solid (514 mg, 96%). H NMR (400 MHz, DMSO): δ 8.22 (d, J = 2.0 Hz, 1 H), 7.91-7.89 (m, 2 H), 7.81- 7.73 (m, 3 H), 7.32 (dd, J = 8.8, 8.8 Hz, 2 H). OH not observed. |
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