Cesium carbonate → HCID 69558529, compound

Participants

Reaction Steps

8-Chloro-2-[5-(3-morpholinopropoxy)-1H-benzimidazol-1-yl]-quinoline 138D (226 mg, 0.53 mMol), racemic-BINAP (50 mg, 0.08 mMol), Cs2CO3 (243 mg, 0.75 mMol), piperidin-4-yl-carbamic acid tert-butyl ester (214 mg, 1.07 mMol), xylenes (1 mL), and Pd(OAc)2 (12 mg, 0.053 mMol) were combined under argon and heated at reflux for 2 days. After allowing the mixture to cool, hexanes were added and decanted off, several times, to remove hexane solubles. The residue was stirred with EtOAc and filtered, and the solids washed with additional EtOAc. The combined EtOAc solutions were evaporated, and the residue chromatographed on silica gel with EtOAc/MeOH elution. Fractions containing the title product 138E were combined and concentrated to provide 130 mg.

Provenance & Evidence