Benzenesulfonyl chloride → 1-benzenesulfonyl-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

온도

0 °C

To a solution of tetrabutylammonium bromide (104 mg, 0.32 mmol) and 5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (1.74 g, 10.76 mmol) in dichloromethane (100 mL) was added sodium hydroxide powder (1.3 g, 32.4 mmol) at 0° C. The mixture was stirred at 0° C. for 5 min and then treated with benzene sulfonyl chloride (1.7 mL, 14.0 mmol). The mixture was stirred at 0° C. for another 15 min before it was warmed to 25° C. and stirred for 12 h. The resulting mixture was filtered and then concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes) afforded 1-benzenesulfonyl-5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (1.54 g, 47.5%) as a white solid: LC/MS m/e calcd for C15H14N2O3S [M+H]+ 303.35, observed 302.9.

1. stirringThe mixture was stirred at 0° C. for another 15 min before it
2. temperaturewas warmed to 25° C.
3. stirringstirred for 12 h
4. filtrationThe resulting mixture was filtered
5. concentrationconcentrated in vacuo
6. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 25% ethyl acetate/hexanes)

ORD 기록

ord-3b32470ce88e4ef09bd0a6dc32046745

출처 데이터셋

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08222416B2