Hydrochloric Acid → HCID 71743058, Verbindung

Temperatur

-40 °C

To a solution of 4-bromo-1-chloro-6-methoxyisoquinoline (0.25 g, 0.917 mmol) in THF (30 ml) was added n-Butyl Lithium (1.147 ml, 1.835 mmol) at −78° C. under nitrogen. The reaction mixture was stirred for 30 minutes and Triisopropyl borate (0.426 ml, 1.835 mmol) was added and stirred for another 30 minutes. To this Hydrogen Peroxide (0.273 ml, 8.90 mmol) (30% solution 1.5M) was added followed by the addition of sodium hydroxide (0.917 ml, 0.917 mmol). The resulting mixture was stirred for additional 1 h at room temperature. The reaction mixture was cooled to −40° C. and added sodium sulfite solution in water (1.156 g, 9.17 mmol). The resulting slurry was neutralized with 6N HCl solution and extracted with ethyl acetate. The combine organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether) to get desired compound (0.13 g, 67.6%) as solid. MS: MS m/z 210.06 (M++1).

1. stirringstirred for another 30 minutes
2. stirringThe resulting mixture was stirred for additional 1 h at room temperature
3. extractionextracted with ethyl acetate
4. dry with materialThe combine organic layer was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customto get crude compound
8. customThe crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether)

ORD-Eintrag

ord-8e929974ffb249599132af80c87ecd56

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08957203B2