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

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-dimethylamino-4-(thiophen-2-yl)-1-(5-(triethylsilyl)pent-4-inyl)cyclohexanol (3.00 g, 7.4 mmol), 2-iodoaniline (1.94 g, 8.9 mmol), [1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)-chloride (PEPPSI, 503 mg, 0.74 mmol) and sodium carbonate (3.92 g, 37 mmol) was evacuated for 30 min (oil pump). It was then flushed with argon and absolute N,N-dimethylformamide (10 mL, previously flushed for 1 h with argon) was added by syringe via a Schlenk tube. The reaction 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 (3×30 mL) and concentrated to low volume again in each case. The residue was distributed between water and ethyl acetate (100 mL each), the phases were separated and the aqueous phase extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with 1 M sodium thiosulphate solution and saturated sodium chloride solution (50 mL each), dried with sodium sulphate and concentrated to low volume in a vacuum. The residue (4.40 g) was purified by means of flash chromatography (200 g, 20×5.7 cm) with dichloromethane/methanol (95:5).

Provenance & Evidence