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. Reaction mixture was warmed to room temperature and allowed to stir for 4 hours. 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 a total of 25 g of the title compound, which was used without further purification. MS (DCI+) m/z 196.9 (M+H)+.

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

ORD record

ord-8dc0df02c0b14123b5565ff6f72b4670

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08435980B2