Sodium Carbonate → 4-Dimethylamino-4-(3-fluorophenyl)-1-[3-(2-(triethylsilyl)-1h-indol-3-yl)propyl]cyclohexanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-dimethylamino-4-(3-fluorophenyl)-1-(5-(triethylsilyl)pent-4-inyl)cyclohexanol (970 mg, 2.32 mmol), 2-iodoaniline (609 mg, 2.78 mmol), [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)-chloride (PEPPSI, 156 mg, 0.23 mmol) and sodium carbonate (1.23 g, 11.6 mmol) was degasified, mixed with oxygen-free N,N-dimethylformamide (10 mL) in argon and stirred for 7 h at 100° C. The reaction mixture was then concentrated to low volume in a vacuum, the residue repeatedly taken up in toluol (10 mL) and concentrated to low volume in a vacuum again each time. This residue was distributed between ethyl acetate (30 mL) and water (30 mL), the organic phase was washed with water (2×15 mL) and sodium thiosulphate solution (2×15 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product was purified by means of flash chromatography (100 g, 20×4.0 cm) with cyclohexane/ethyl acetate (4:1).

Provenance & Evidence