Sodium Carbonate → (R)-4-dimethylamino-1-[2-methyl-3-(2-(triethylsilyl)-1H-indol-3-yl)propyl]-4-phenylcyclohexanol

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Reaction Steps

A solution of (R)-4-dimethylamino-1-(2-methyl-5-(triethylsilyl)pent-4-inyl)-4-phenylcyclohexanol (106 mg, 0.25 mmol), [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)-chloride (PEPPSI, 34 mg, 0.05 mmol), 2-iodoaniline (68 mg, 0.31 mmol) and sodium carbonate (136 mg, 1.28 mmol) in oxygen- and water-free N,N-dimethylformamide (5 mL) was stirred for 18 h at 100° C. The reaction mixture was concentrated to low volume in a vacuum, the residue mixed with toluol several times and the mixture concentrated to low volume again in each case. This residue was distributed between water and ethyl acetate (10 mL each), the phases were separated and the aqueous phase extracted with ethyl acetate (3×10 mL). The combined organic phases were washed with 1 M sodium thiosulphate solution and water (10 mL each), dried with sodium sulphate, filtered and concentrated to low volume in a vacuum. The raw product was purified by flash chromatography (10 g, 20×1.5 cm) with ethyl acetate/cyclohexane (1:2).

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