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

Participants

Reaction Steps

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).

Provenance & Evidence