Ethanol → 3-(4,5-Diamino-2'-trifluoromethyl-biphenyl-3-yl)-prop-2-en-1-ol

Temperature

80 °C

3-(4-Amino-5-nitro-2′-trifluoromethyl-biphenyl-3-yl)-prop-2-yn-1-ol (131 mg, 0.390 mmol, as prepared in Example 10, step A) was placed in an 8 mL vial equipped with a magnetic stir bar, and EtOH (4 mL) was added via syringe followed by water (1 mL). Ammonium chloride (10 eq., 209 mg, 3.90 mmol) and Fe powder (5 eq., 109 mg, 1.95 mmol) were added as solids. The vial was tightly capped, placed in a heated block, and stirred at 80° C. for 16 h. The reaction was cooled to RT, filtered, and the solids were washed three times with MeOH (5 mL). The filtrate was concentrated under reduced pressure, the residue was dissolved in EtOAc (20 mL) and washed with water (20 mL), and the aqueous layer was extracted three times with EtOAc (10 mL). The combined organic extracts were washed with brine (20 mL), dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure, yielding 95 mg of the title compound as a 1:1 mixture with 3-(4,5-diamino-2′-trifluoromethylbiphenyl-3-yl)-prop-2-yn-1-ol. The mixture was carried through to the next step.

1. customvial equipped with a magnetic stir bar
2. customThe vial was tightly capped
3. temperatureThe reaction was cooled to RT
4. filtrationfiltered
5. washthe solids were washed three times with MeOH (5 mL)
6. concentrationThe filtrate was concentrated under reduced pressure
7. dissolutionthe residue was dissolved in EtOAc (20 mL)
8. washwashed with water (20 mL)
9. extractionthe aqueous layer was extracted three times with EtOAc (10 mL)
10. washThe combined organic extracts were washed with brine (20 mL)
11. dry with materialdried over anhydrous MgSO4
12. filtrationfiltered
13. customthe solvent was removed under reduced pressure

ORD record

ord-2baa81c12dcb45c2bb2ac5d57cfa0305

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232409B2