Hexane → 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-ethanol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a suspension of 1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridine (1.0 g, 3.62 mmol) in dry tetrahydrofuran (30 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (1.6M, 2.72 mL, 4.35 mmol). The mixture was stirred at −78° C. for 5 min and then treated with (tetrahydro-pyran-4-yl)-acetaldehyde (0.7 g, 5.43 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched with brine. The mixture was extracted with ethyl acetate (2×100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (QingDao silica gel, 200-300 mesh, 25% ethyl acetate/hexanes) afforded 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-ethanol (1.23 g, 84%): LC/MS m/e calcd for C20H21FN2O4S [M+H]+ 405.46, observed 405.2.

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