Methanol → 2-(7-fluoro-1H-benzimidazol-1-yl)ethanol

To a solution of 2-[(2-fluoro-6-nitrophenyl)amino]ethanol (0.78 g ) in methanol (15 mL) 10% palladium on carbon (200 mg) was added. The mixture was hydrogentated at hydrogen pressure 1 bar until the consumption of hydrogen gas ceased (60 min). The reaction mixture was filtered through a pad of Celite, which was further washed with methanol and acetonitrile. The filtrate was concentrated to dryness and the residue was dissolved in formic acid (4 mL). The solution was transferred into a microwave vial, which was sealed and irradiated for 15 min at 135° C. The solvent was removed in vacuum, the residue was dissolved in methanol (4 mL) and a 7 M solution of ammonia in methanol (4 mL) was added. After 10 min the mixture was concentrated to dryness and the residue was purified on a short silica column. Yield 0.65 g (93%). MS (ESI) m/z 181.1 [M+H]. 1H NMR (400 MHz, DMSO-D6) δ ppm: 3.60 (t, J=5.3 Hz, 2H), 4.21 (t, J=5.3 Hz, 2H), 6.92 (dd, J=12.1, 8.1 Hz, 1H), 7.02 (m, 1H), 7.34 (d, J=8.1 Hz, 1H), 8.03 (s, 1H), 8.26 (s, 1H).

1. customThe mixture was hydrogentated at hydrogen pressure 1 bar until the consumption of hydrogen gas
2. custom(60 min)
3. filtrationThe reaction mixture was filtered through a pad of Celite, which
4. washwas further washed with methanol and acetonitrile
5. concentrationThe filtrate was concentrated to dryness
6. dissolutionthe residue was dissolved in formic acid (4 mL)
7. customwas sealed
8. customirradiated for 15 min at 135° C
9. customThe solvent was removed in vacuum
10. dissolutionthe residue was dissolved in methanol (4 mL)
11. additiona 7 M solution of ammonia in methanol (4 mL) was added
12. concentrationAfter 10 min the mixture was concentrated to dryness
13. customthe residue was purified on a short silica column

ORD record

ord-7b5480ba4141431c9243498ae7330fed

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07645784B2