Iodoethane → 1-Benzenesulfonyl-4-bromo-2-ethyl-1H-pyrrolo[2,3-c]pyridine

Temperature

-35 °C

To a solution of 1-benzenesulfonyl-4-bromo-1H-pyrrolo[2,3-c]pyridine (0.63 g, 1.86 mmol) in anhydrous THF (10 mL), at −35° C., was added a solution of lithium diisopropylamide (2.0M in heptane/THF/ethyl benzene, 1.86 mL, 3.77 mmol) dropwise. The reaction mixture was stirred at −35° C. for 30 min and then ethyl iodide (0.90 mL, 11.18 mmol) was added dropwise. The resulting solution was allowed to reach room temperature and was stirred for 4 h. The reaction mixture was quenched by addition of a solution of 1N HCl (5 mL); the solution was diluted with water (15 mL) and extracted with EtOAc (2×75 mL). The organic extracts were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, EtOAc:cyclohexane 0:100 to 70:30). The residue was triturated in EtOAc (2 mL) and collected by filtration to give the title compound as a white solid (0.27 g, 40%). LCMS (Method H): RT=4.65 min, [M+H]+ 367 (79Br), 369 (81Br)

1. customto reach room temperature
2. stirringwas stirred for 4 h
3. customThe reaction mixture was quenched by addition of a solution of 1N HCl (5 mL)
4. additionthe solution was diluted with water (15 mL)
5. extractionextracted with EtOAc (2×75 mL)
6. washwashed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in vacuo
9. customThe residue was purified by flash chromatography (Si—PPC, EtOAc:cyclohexane 0:100 to 70:30)
10. customThe residue was triturated in EtOAc (2 mL)
11. filtrationcollected by filtration

ORD record

ord-5b6639b272bc485fae1b5ccd1b8699c9

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394796B2