反应详情

To a suspension of 1H-pyrrolo[2,3-c]pyridine (700 mg, 5.9 mmol) in tetrahydrofuran (14.0 mL) was added lithium diisopropylamide (2.9 mL of a 2 M solution in THF/heptane, 5.9 mmol) at −78° C. After 0.5 h, benzenesulfonyl chloride (0.79 mL, 6.2 mmol) was added dropwise. The mixture was allowed to slowly warm to ambient temperature overnight. The reaction mixture was poured into 2% aq NaHCO3 (30 mL) and extracted with EtOAc (2×25 mL). The combined extracts were washed with H2O (20 mL) and saturated NaCl (20 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, 1:1 hexanes/EtOAc) gave 1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine (1.2 g, 80%): 1H NMR (500 MHz, DMSO-d6) δ 6.94 (1H, d, J=6.0 Hz), 7.59-7.66 (3H, m), 7.70-7.75 (1H, m), 8.07-8.10 (3H, m), 8.38 (1H, d, J=8.8 Hz), 9.23 (1H, s); ESI MS m/z 259 [C13H10N2O2S+H]+.

1. extractionextracted with EtOAc (2×25 mL)
2. washThe combined extracts were washed with H2O (20 mL) and saturated NaCl (20 mL)
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated under reduced pressure
5. customPurification by column chromatography (silica gel, 1:1 hexanes/EtOAc)