Tetrahydrofuran → 6-fluoro-1-(propan-2-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one

A mixture of (5-fluoro-2-nitrophenyl)isopropylamine (Step 1 of Example 9, 5.85 g, 30 mmol) and 10% Pd—C (600 mg) in MeOH was stirred under atmosphere of hydrogen gas at room temperature for 12 h. The catalyst was filtered off on a pad of Celite, and the filtrate was evaporated under reduced pressure. To the residue was added 1,1′-carbonyldiimidazole (4.5 g, 28 mmol) and THF (100 μL) and then stirred at 100° C. for 10 h. After cooling, the volatile materials were removed under reduced pressure and the residue was partitioned between ethylacetate and H2O. After extraction with ethylacetate (3 times), the combined organic phase was washed with brine, dried over MgSO4 and concentrated. The residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (2:1) to give 3.47 g (60%) of the title compound as a white solid.

1. filtrationThe catalyst was filtered off on a pad of Celite
2. customthe filtrate was evaporated under reduced pressure
3. stirringstirred at 100° C. for 10 h
4. temperatureAfter cooling
5. customthe volatile materials were removed under reduced pressure
6. customthe residue was partitioned between ethylacetate and H2O
7. extractionAfter extraction with ethylacetate (3 times)
8. washthe combined organic phase was washed with brine
9. dry with materialdried over MgSO4
10. concentrationconcentrated
11. customThe residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (2:1)

ORD record

ord-e11beea3f09b41e083e78137a1f50fe5

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07776885B2