Potassium Hydroxide → HCID 68157225, compound

Temperature

90 °C

To a solution of (2-bromo-3-fluoro-6-nitrophenyl)phenylamine (1.5 g, 4.8 mmol) in dioxane (20 mL) and water (10 mL) was added tris(dibenzylideneacetone)dipalladium (0) (88 mg, 0.96 mmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (164 mg, 0.39 mmol) and potassium hydroxide (812 mg, 14.4 mmol). The reaction mixture was degassed by bubbling argon through the mixture whilst undergoing sonication. The reaction mixture was heated at 90° C. for 3 h before being diluted with water and acidified to ˜pH 3 by addition of HCl (1N). The mixture was extracted with EtOAc (3×20 mL). The combined organic fractions were washed with brine, dried (MgSO4), concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane) to give the title compound as a yellow solid (879 mg, 59%). 1H NMR 400 MHz 6 (CDCl3): 8.85 (1H, br s), 8.18 (1H, d, J=12.6 Hz), 7.31-7.24 (2H, m), 7.10-7.03 (1H, m), 6.92-6.86 (2H, m), 6.80 (1H, d, J=12.6 Hz).

1. customThe reaction mixture was degassed
2. customby bubbling argon through the mixture
3. customsonication
4. additionbefore being diluted with water
5. additionby addition of HCl (1N)
6. extractionThe mixture was extracted with EtOAc (3×20 mL)
7. washThe combined organic fractions were washed with brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo
10. washthe resultant residue subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane)

ORD record

ord-5239ba6e7aa14396b1cae36d7dc972f7

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2