1H-Pyrrolo(2,3-b)pyridine → 3-Bromo-1H-pyrrolo[2,3-b]pyridine

To a solution of 1H-pyrrolo[2,3-b]pyridine (15.6 g, 132 mmol) in 400 mL tetrahydrofuran at −40° C. was added a suspension of N-bromosuccinimide in 120 mL tetrahydrofuran. The reaction mixture was warmed to room temperature and allowed to stir for 4 hours. The solid was filtered off. The reaction mixture was quenched with a sodium metabisulfite solution, and extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was triturated with 1:1 hexane/ethyl acetate and filtered. The filtrate was concentrated and the trituration step was repeated three more times to afford the title compound, which was used without further purification. MS (DCI−) m/z 196.9 (M+H)+.

1. filtrationThe solid was filtered off
2. customThe reaction mixture was quenched with a sodium metabisulfite solution
3. extractionextracted with ethyl acetate
4. washThe combined organics were washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was triturated with 1:1 hexane/ethyl acetate
9. filtrationfiltered
10. concentrationThe filtrate was concentrated

ORD record

ord-351994e662ef42da9079f53aefb42b0b

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383623B2