Sodium Chloride → HCID 86689178, compound

Participants

Reaction Steps

3-Fluoro-4-(8-hydroxy-7-methoxy-3-methyl-2-oxo-2,3-dihydroimidazo[4,5-c]quinolin-1-yl)benzonitrile (350 mg, 961 μmol) and diphenyl-2-pyridylphosphine (1.46 g, 5.39 mmol) were dissolved in tetrahydrofuran (105 ml). 2-Trimethylsilanylethyl(2-hydroxy-2-thiophen-2-ylethyl)carbamate (787 mg, 2.74 mmol) and diisopropyl azodicarboxylate (788 μl, 4.01 mmol) were subsequently added. The reaction mixture was stirred at room temperature for 15 min. When the reaction was complete (HPLC-MS), it was added to ethyl acetate (50 ml) and saturated sodium chloride solution (50 ml) and extracted. The aqueous phase was extracted with further ethyl acetate (25 ml). The combined organic phases were washed with water (25 ml), dried over Na2SO4 and filtered. The filtrate was evaporated to dryness in vacuo, and the residue was chromatographed over flash silica gel (solvent gradient ethyl acetate/0-7% by vol. of ethanol), giving 2-trimethylsilanylethyl {2-[1-(4-cyano-2-fluorophenyl)-7-methoxy-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yloxy]-2-thiophen-2-ylethyl}carbamate (253 mg, 399 μmol) as solid. MS: 634.2 (M+H+), TLC (HPTLC): Rf=0.34 (ethyl acetate/ethanol 8:1, parts by volume).

Provenance & Evidence