反应详情

温度

80 °C

A sealed tube containing the mixture of methyl 2-(4-chloro-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylate (390 mg, 1.10 mmol), potassium 1-trifluoroboratom-ethylpyrrolidine (158; 212 mg, 1.11 mmol), Pd (OAc)2 (22 mg, 0.03 mmol), XPhos (31 mg, 0.06 mmol), and cesium carbonate (1.0 g, 3.3 mmol) was evacuated and filled with nitrogen twice. To the mixture was added THF/H2O (10:1, 4.4 mL). The suspension was heated at 80° C. overnight and cooled to room temperature. Water (2 mL) was added and the reaction was extracted with CH2Cl2 twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. Purification by silica gel chromatography (MeOH/CH2Cl2+1% Et3N) afforded methyl 2-(4-(pyrrolidin-1-ylmethyl)-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylate (structure not shown) as a yellow solid (544 mg).

1. additionA sealed tube containing
2. customwas evacuated
3. additionfilled with nitrogen twice
4. additionTo the mixture was added THF/H2O (10:1, 4.4 mL)
5. temperaturecooled to room temperature
6. additionWater (2 mL) was added
7. extractionthe reaction was extracted with CH2Cl2 twice
8. washThe combined organic layers were washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. customPurification by silica gel chromatography (MeOH/CH2Cl2+1% Et3N)