Hydrochloric Acid → HCID 53415940, compound

3-fluorophenylboronic acid (0.5 g; 3.6 mmol), bromocyclopentane (0.41 g; 2.7 mmol), potassium tert-butoxide (0.49 g; 4.3 mmol), bathophenanthroline (72 mg; 0.22 mmol), bis(1,5-cyclooctadiene)nickel(0) (30 mg; 0.11 mmol) and t-butanol (9 mL) were added sequentially to a 10-20 mL microwave reactor tube containing a stir bar. The vessel was capped, placed under nitrogen, and then subjected to the following microwave conditions: Temperature=160° C.; Time=5 minutes; Power=250 W; Cooling turned on; Absorption=High; prestir=5 s; FHT turned off. The crude reaction mixture was allowed to cool to room temperature and then acidified by the addition of aqueous hydrochloric acid (15 mL; 1N) and extracted with ethyl acetate (3×20 mL). The combined organic phases were successively washed with aqueous saturated sodium bicarbonate, aqueous saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting crude residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes to give the title product as a light red solid (0.2 g).

1. additioncontaining a stir bar
2. customThe vessel was capped
3. customTemperature=160° C.
4. customTime=5 minutes
5. temperatureCooling
6. customAbsorption=High
7. customThe crude reaction mixture
8. extractionextracted with ethyl acetate (3×20 mL)
9. washThe combined organic phases were successively washed with aqueous saturated sodium bicarbonate, aqueous saturated sodium chloride
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customThe resulting crude residue was purified by automated silica gel column chromatography (Biotage®)
14. washeluting with ethyl acetate/hexanes

ORD record

ord-67ee7c4c99994fe2ad1e62c26d49cc2a

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178699B2