Dichloromethane → HCID 45376884, compound

Participants

Reaction Conditions

Reaction Steps

A pressure vial is charged with 5-bromo-2-pyridin-4-ylmethyl-1H-benzimidazole-1-carboxylic acid tert-butyl ester (100 mg, 0.26 mmol), bis(pinacolato)diboron (72 mg, 0.28 mmol), KOAc (99 mg, 1.01 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (PdCl2(dppf)*CH2Cl2) (8.2 mg, 0.01 mmol). After flushing with nitrogen, DME (2 mL) is added and the reaction stirred at 100° C. for 2 h. The mixture is cooled to room temperature before 5-bromo-furan-2-carboxylic acid ((S)-cyclohexyl-methylcarbamoyl-methyl)-amide (88 mg, 0.26 mmol), PdCl2(dppf)*CH2Cl2 (8.2 mg, 0.01 mmol), and 2M Na2CO3 solution (0.84 mL, 1.68 mmol) are added. The mixture is stirred at 110° C. for 8 h. Water is added and the mixture is extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4. After removal of the solvent, the residue was purified by reversed phase (HPLC). The product is obtained as a pale yellow solid. 19 mg, 15%, LC/MS ESI m/z (M+H)+=472.46

Provenance & Evidence