N,N-Dimethylformamide--water (1/1) → HCID 66705772, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 60 mg (0.104 mmol) of 3-{3-[(S)-{3-[(1S)-1-(3-bromo-5-fluorophenyl)-2-fluoro-2-methyl propyl]azetidin-1-yl}(4-chlorophenyl)methyl]phenyl}-1,2,4-oxadiazole, 48.5 mg (0.84 mmol) of zinc cyanide, 4 mg (0.004 mmol) of tris(dibenzylideneacetone)-dipalladium, and 5 mg (0.009 mmol) of DPPF in 3 mL of DMF/H2O (99/1) was degassed with N2 for 1 h at rt. Then it was stirred at 135° C. After 14 h, the reaction mixture was concentrated to remove solvents. Then the mixture was poured into 20 mL of CH2Cl2 and 5 mL of aq NaHCO3 (pH>7). The aqueous layer was extracted with CH2Cl2 and the combined organic layer was dried over Na2S04 and concentrated. The residue was purified by silica gel chromatography with hexanes/acetone to afford the title compound as a white solid; Mass Spectrum: m/e=519 (M+1, 35Cl), 521 (M+1, 37Cl).

Provenance & Evidence