Dimethylformamide → HCID 11372931, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,7-dibromofluoren-9-one (1.00 g, 2.97 mmol; Aldrich), 3-diethylamino-1-propyne (1.6 mL, 11.6 mmol; Lancaster), triethylamine (2 mL, 14.4 mmol; Acros), dichlorobis(triphenylphosphino)palladium(II) (Cl2Pd(PPh3)2; 90 mg, 0.13 mmol; Aldrich), and copper(I) iodide (130 mg, 0.68 mmol; Aldrich) in DMF (30 mL) was heated to 65° C. for 60 h. The reaction mixture was diluted with EtOAc, washed with water and brine, and dried over Na2SO4. The residue was purified twice by chromatography (80 g silica gel, eluting with 2-7% of 10% NH4OH/MeOH in CH2Cl2, followed by 80 g silica gel, 1-6% MeOH-CH2Cl2) to afford the title compound (1.12 g, 2.81 mmol, 95% yield). MS (DCl/NH3) m/z 399 (M+H)+.

Provenance & Evidence