Sodium Carbonate → 4-dimethylamino-4-phenyl-1-[3-(2-triethylsilanyl-1H-pyrrolo[3,2-c]pyridin-3-yl)propyl]cyclohexanol

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-dimethylamino-4-phenyl-1-(5-triethylsilanyl-pent-4-inyl)cyclohexanol (741 mg, 1.85 mmol), 4-amino-3-iodopyridine (488 mg, 2.22 mmol), [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)-chloride (PEPPSI, 251 mg, 0.37 mmol) and sodium carbonate (980 mg, 9.25 mmol) in oxygen-free N,N-dimethylformamide (10 mL) was stirred for 20 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 each time concentrated to low volume again in a vacuum, this residue was taken up in ethyl acetate (30 mL) and water (30 mL) and the organic phase washed with water (2×15 mL) and sodium thiosulphate solution (2×25 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product was purified by means of flash chromatography (38 g, 20×2.5 cm) with ethyl acetate/methanol (4:1).

Provenance & Evidence