Potassium Carbonate → 9-Methyl-6h-11-oxa-6,10-diaza-benzo[a]fluoren-5-one

Temperature

100 °C

To a solution of α-bromodimethylhomophthalate (2.00 g, 6.97 mmol) in DMF (15 mL) was added 3-cyano-2-hydroxy-6-methylpyridine (1.03 g, 1.1 eq) and potassium carbonate (4.82 g, 5 eq). The resulting mixture was allowed to stir at 100° C. for 4 h under inert atmosphere. The reaction was cooled to room temperature and concentrated in vacuo. The resulting solid residue was diluted with 1 N aqueous HCl (60 mL) and stirred for 30 min. The resulting suspension was filtered and the solids were washed with water. The aqueous filtrate was extracted with EtOAc (2×50 mL). The collected solids were added to the combined EtOAc extracts, and the resulting solution was dried over sodium sulfate, filtered and concentrated in vacuo to afford a crude residue. The crude residue was recrystallized from toluene at −20° C. over 18 h, vacuum filtered and dried to provide compound 26a as a yellow solid. Yield=500 mg (29%).

1. temperatureThe reaction was cooled to room temperature
2. concentrationconcentrated in vacuo
3. additionThe resulting solid residue was diluted with 1 N aqueous HCl (60 mL)
4. stirringstirred for 30 min
5. filtrationThe resulting suspension was filtered
6. washthe solids were washed with water
7. extractionThe aqueous filtrate was extracted with EtOAc (2×50 mL)
8. additionThe collected solids were added to the combined EtOAc
9. dry with materialthe resulting solution was dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customto afford a crude residue
13. customThe crude residue was recrystallized from toluene at −20° C. over 18 h
14. filtrationvacuum filtered
15. customdried

ORD record

ord-1d8373a1a78c4bd7b87a85f48fef35bf

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07217709B2