Ammonium Chloride → 1-(3-(trifluoromethyl)benzyl)-1H-indazol-4-amine

To a round bottom flask was added 3-iodo-4-nitro-1-(3-(trifluoromethyl)benzyl)-1H-indazole (0.540 g, 1.21 mmol) and MeOH (12 mL). Zinc dust (0.395 g, 6.04 mmol) was added followed by saturated aqueous NH4Cl (12 mL). The mixture was stirred vigorously at ambient temperature for 2 hours. The reaction mixture was filtered and the solids were washed with EtOAc (30 mL). Saturated aqueous NH4OAc (25 mL) was added to the filtrate and the mixture was concentrated to remove organic solvents. The aqueous phase was then extracted with EtOAc (3×20 mL). The combined organic extracts were washed with a saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified by 1 mm preparative TLC using 5% MeOH/CH2Cl2 to afford 0.120 g (34%) of the product as a dark yellow/orange oil.

1. filtrationThe reaction mixture was filtered
2. washthe solids were washed with EtOAc (30 mL)
3. additionSaturated aqueous NH4OAc (25 mL) was added to the filtrate
4. concentrationthe mixture was concentrated
5. customto remove organic solvents
6. extractionThe aqueous phase was then extracted with EtOAc (3×20 mL)
7. washThe combined organic extracts were washed with a saturated aqueous NaHCO3 solution and brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude residue was purified by 1 mm preparative TLC

ORD record

ord-5823ec072923445a8d3af5cebf1db7a0

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174981B2