Formic Acid → 2-(7-chloro-6-fluoro-1H-benzimidazol-1-yl)ethanol

Temperature

100 °C

2-[(6-Amino-2-chloro-3-fluorophenyl)amino]ethanol (2.07 g, 10.2 mmol) is dissolved in formic acid (50.0 mL), and the resulting solution is heated to 100° C. for 1 hour. The solution is cooled to room temperature and then evaporated to dryness. The residue is suspended in NH3 (50.0 mL, 2N in EtOH) and stirred for 1 hour. The solution is concentrated to dryness, and the residue is suspended in EtOAc (50.0 mL). The organic phase is washed with 2N NaOH (50.0 mL), and the resulting aqueous phase is extracted 4 times with EtOAc (4×50.0 mL). The combined organic phases are dried with MgSO4, filtered and concentrated. The product is dissolved in EtOAc, filtered and recrystallized from EtOAc (895 mg, 41%). 1H NMR (400 MHz, DMSO-D6) δ ppm 3.74 (t, J=5.27 Hz, 2H) 4.52 (t, J=5.47 Hz, 2H) 4.99 (s, 1H) 7.25 (dd, J=10.16, 8.79 Hz, 1H) 7.64 (dd, J=8.79, 4.49 Hz, 1H) 8.21 (s, 1H).

1. temperatureThe solution is cooled to room temperature
2. customevaporated to dryness
3. concentrationThe solution is concentrated to dryness
4. washThe organic phase is washed with 2N NaOH (50.0 mL)
5. extractionthe resulting aqueous phase is extracted 4 times with EtOAc (4×50.0 mL)
6. dry with materialThe combined organic phases are dried with MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. dissolutionThe product is dissolved in EtOAc
10. filtrationfiltered
11. customrecrystallized from EtOAc (895 mg, 41%)

ORD record

ord-3d9391639a1944a698369a274f3a95bf

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093402B2