Sodium Carbonate → 4-dimethylamino-1-[3-(5-fluoro-2-triethylsilanyl-1H-indol-3-yl)propyl]-4-phenylcyclohexanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-dimethylamino-4-phenyl-1-(5-triethylsilanyl-pent-4-inyl)cyclohexanol (525 mg, 1.31 mmol), 4-fluoro-2-iodoaniline (374 mg, 1.58 mmol), [1,3-bis-(2,6-diisopropyl-phenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)-chloride (PEPPSI, 178 mg, 0.26 mmol) and sodium carbonate (694 mg, 6.6 mmol) was evacuated for 30 min (oil pump). It was then flushed with argon and absolute N,N-dimethylformamide (5 mL, previously flushed for 1 h with argon) was added by syringe via a Schlenk tube. The mixture was stirred for 18 h at 100° C. and changed colour to dark brown during this. The reaction mixture was then concentrated to low volume in a vacuum, the residue taken up several times in toluol (3×10 mL) and concentrated to low volume again in each case, distributed between water and ethyl acetate (20 mL each) and the phases separated again. The aqueous phase was extracted with ethyl acetate (2×30 mL), the combined organic phases were washed with 1 M sodium thiosulphate solution (30 mL) and saturated sodium chloride solution (50 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product (1.10 g) was purified by means of flash chromatography (50 g, 20×3.0 cm) with chloroform/methanol (97:3).

Provenance & Evidence