Methanol → HCID 86687422, compound

Temperature

50 °C

A round bottom flask was charged with 6-bromo-2h-isoquinolin-1-one (5.0 g, 22.32 mmol) and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor®) (9.49 g, 26.8 mmol, Air Products, Allentown, Pa.). Methanol (55.8 ml) and acetonitrile (55.8 ml) were added and the reaction was heated to 50° C. and stirred for one hour. The reaction was concentrated, dissolved in DCE (110 mL), and POCl3 (4.16 ml, 44.6 mmol) was added. The reaction was stirred at 50° C. for one hour. The reaction was quenched into ice water and extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered, and concentrated to afford crude 6-bromo-4-fluoroisoquinolin-1(2H)-one as a light pink solid. (ESI) 242.1 (M+H)+.

1. concentrationThe reaction was concentrated
2. dissolutiondissolved in DCE (110 mL)
3. stirringThe reaction was stirred at 50° C. for one hour
4. customThe reaction was quenched into ice water
5. extractionextracted with ethyl acetate
6. dry with materialThe combined organic layers were dried with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-29e23aac9c2a48abaec297d2bb29200b

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012443B2