2-Bromoethanol → HCID 11583718, compound

Participants

Reaction Steps

55 mg (0.40 mmol) of potassium carbonate and 28 μL (0.40 mmol) of 2-bromoethanol was added to a solution of 86.2 mg (0.20 mmol) of (2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethyl)cyclopentylamine in 2 mL of DMF and the mixture was stirred for 24 hours at RT. Another 55 mg (0.40 mmol) of potassium carbonate and 28 μL (0.40 mmol) of 2-bromoethanol were added and the mixture was stirred for 8 hours at 50° C. The reaction mixture was evaporated down in vacuo and the residue was taken up in DCM. The organic phase was washed with water, dried over sodium sulfate, and evaporated down in vacuo. The crude product was purified by MPLC (silica gel, EtOAc/MeOH 95:5) and then MPLC (Alox, cyc/EtOAc 8:2) and triturated with DIPE. Yield: 2.9 mg (3% of theoretical); C29H31ClN2O2 (M=475.021); calc.: molpeak (M+H)+: 475/477 (Cl); found: molpeak (M+H)+: 475/477 (Cl); Rf value: 0.26 (silica gel, EtOAc/MeOH 95:5)

Provenance & Evidence