Benzenesulfonyl chloride → 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Temperature

0 °C

To a solution of 1H-pyrrolo[2,3-b]pyridine (20 g, 169 mmol, (available from, for example Sigma Aldrich) in tetrahydrofuran (THF) (250 mL) was added sodium hydride (10.16 g, 254 mmol) portionwise during 5 min under nitrogen at 0° C. The reaction mixture was stirred at 0° C. for 30 min, then benzenesulfonyl chloride was added dropwise under nitrogen at 0° C. then stirred for 2 h at r.t., until the starting material had been completely consumed (TLC, EtOAc:PE=1:1). The mixture was poured into H2O (200 mL) and extracted with EtOAc (3×200 mL). The organic layers were washed with brine (3×150 mL), dried over Na2SO4 and filtered. The solvent was evaporated in vacuo to give the crude product, which was purified by recrystallization with (EtOAc and PE) to give desired product as a white solid (30 g, 69%)

1. customportionwise during 5 min
2. customat 0° C
3. stirringthen stirred for 2 h at r.t., until the starting material
4. customhad been completely consumed (TLC, EtOAc:PE=1:1)
5. additionThe mixture was poured into H2O (200 mL)
6. extractionextracted with EtOAc (3×200 mL)
7. washThe organic layers were washed with brine (3×150 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. customThe solvent was evaporated in vacuo
11. customto give the crude product, which
12. customwas purified by recrystallization with (EtOAc and PE)

ORD record

ord-7eaf24e2e0704e12ba71ecd33bd583eb

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09127003B2