Potassium Hydroxide → HCID 68157225, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence