Methyl iodide → 1-Benzenesulfonyl-4-bromo-2-methyl-1H-pyrrolo[2,3-c]pyridine

Temperature

-35 °C

To a solution of 1-benzenesulfonyl-4-bromo-1H-pyrrolo[2,3-c]pyridine (0.96 g, 2.84 mmol) in anhydrous THF (10 mL), at −35° C., was added a solution of lithium diisopropylamide (2.0M in heptane/THF/ethyl benzene, 2.84 mL, 5.68 mmol) dropwise. The mixture was stirred at −35° C. for 45 min and then methyl iodide (1.06 mL, 17.04 mmol) was added dropwise. The resulting solution was allowed to reach room temperature and was stirred for 3 h. The reaction mixture was quenched by addition of an aqueous 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, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, DCM:cyclohexane, gradient 0:100 to 100:0). The residue was triturated in EtOAc (2 mL) and collected by filtration to give the title compound as a white solid (0.39 g, 39%). LCMS (Method A): RT=4.47 min, [M+H]+ 351 (79Br), 353 (81Br)

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

ORD record

ord-98a31971a267498d96f1a963a480b638

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394796B2