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

Temperature

-35 °C

A 50 mL round-bottomed flask, under nitrogen fitted with a thermometer probe, and a condenser/inert gas bubbler (via a Claisen head), was charged with a solution of 1-benzenesulfonyl-4-bromo-1H-pyrrolo[2,3-c]pyridine (0.96 g, 2.84 mmol) in anhydrous THF (10 mL). To the resultant solution, at −35° C., was added dropwise a solution of lithium diisopropylamide (2.0M in heptane/THF/ethyl benzene, 2.84 mL, 5.68 mmol) and the mixture then stirred at −35° C. for 45 min. Methyl iodide (1.06 mL, 17.04 mmol) was added to the reaction mixture dropwise. The resulting solution was allowed to reach room temperature and was stirred for 3 h. The reaction 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 layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, 0-100% DCM:cyclohexane). The residue was triturated with EtOAc (2 mL) and the precipitate was 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. customA 50 mL round-bottomed flask, under nitrogen fitted with a thermometer probe
2. customto reach room temperature
3. stirringwas stirred for 3 h
4. customThe reaction was quenched by addition of a solution of 1N HCl (5 mL)
5. additionthe solution was diluted with water (15 mL)
6. extractionextracted with EtOAc (2×75 mL)
7. dry with materialThe organic layer was dried (Na2SO4)
8. concentrationconcentrated in vacuo
9. customThe residue was purified by flash chromatography (Si—PPC, 0-100% DCM:cyclohexane)
10. customThe residue was triturated with EtOAc (2 mL)
11. filtrationthe precipitate was collected by filtration

ORD record

ord-1f4d5879a46e426aae2370a0507b5c8e

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394796B2