Cesium carbonate → Methyl 2-(4-(pyrrolidin-1-ylmethyl)-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence