Tetrahydrofuran → HCID 58488145, compound

To a stirred mixture of 5,8-dibromoisoquinoline (4.0 g. 13.9 mmol) in tetrahydrofuran (120 mL) at −78° C. under nitrogen atmosphere was added dropwise a solution of n-butyllithium (2.3 M in hexane, 7.3 mL, 16.8 mmol). The reaction mixture turned dark. After stirring for 15 minutes, the reaction mixture was quenched by adding N,N-dimethylformamide (4.0 mL). After stirring at −78° C. for an additional 1 h, the reaction mixture was quenched with water, extracted with mixture of ethyl acetate/hexane (2:8), washed with water and brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using hexanes/ethyl acetate as eluent to afford the 8-bromo-5-isoquinolinecarboxaldehyde (0.10 g), followed by 5-bromo-8-isoquinolinecarboxaldehyde (1.0 g) as white solids.

1. customthe reaction mixture was quenched
2. additionby adding N,N-dimethylformamide (4.0 mL)
3. stirringAfter stirring at −78° C. for an additional 1 h
4. customthe reaction mixture was quenched with water
5. extractionextracted with mixture of ethyl acetate/hexane (2:8)
6. washwashed with water and brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by column chromatography on silica gel

ORD record

ord-4329af261d514707aa8ae3942b8873ee

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871941B2