Methyl iodide → 3-Bromo-1-methyl-7-azaindole

Step 1—A solution of commercially available 3-bromo-1H-pyrrolo[2,3-b]pyridine (0.53 g, 2.69 mmol) in 4 mL of DMF was added at 0° C. to a suspension of NaH 60% dispersion in oil (0.14 g, 3.497 mmol) in 4 mL of DMF. The resulting mixture was stirred at RT for 30 minutes before being cooled to 0° C. and adding iodomethane (0.67 mL, 10.759 mmol). The reaction mixture was allowed to reach RT overnight before being quenched by addition of H2O and extracted three times with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified by SiO2 chromatography (hexanes/EtOAc 0-20% EtOAc) to give 0.386 g of 3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine (68% yield).

1. temperaturebefore being cooled to 0° C.
2. waitto reach RT overnight
3. custombefore being quenched by addition of H2O
4. extractionextracted three times with EtOAc
5. washThe combined organic layers were washed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by SiO2 chromatography (hexanes/EtOAc 0-20% EtOAc)

ORD record

ord-1e9d0b04b12c4d24a65ab2596f7b75a2

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07939531B2