Benzenamine, 2,6-difluoro-N-(2-methylpropyl)- synthesis

Yield:1039932-02-9 80 mg

Reaction Conditions:

with bis[dichloro(pentamethylcyclopentadienyl)iridium(III)];potassium iodide at 190; for 8 h;Microwave irradiation;

Steps:

P170.a a) preparation of 2,6-difluoro-N-(2-methylpropyl)aniline

2,6-difluoroaniline (387 mg, 3 mmol), potassium iodide (996 mg, 6.00 mmol) and [Cp*IrCI₂]2 (33.1 mg, 0.030 mmol) were dissolved in 2-methyl-l-propanol (3 mL, 32.4 mmol). The resulting mixture was heated by microwaves to 190 °C for 8 hours. To the reaction mixture was added dichloromethane (10 mL) and water (10 mL) and the organic phase separated (hydrophobic frit).Diethyl ether was added and the solution filtered through a silica cartridge (10 g) eluting with further diethyl ether. The filtrate was evaporated in vacuo, then purified by flash silica (Si) chromatography (using a 0-100% dichloromethane-cyclohexane gradient). The appropriate fractions were combined and concentrated to give the title product (80 mg) as a colourless oil.LCMS (M+l) 186, RT 1.26 mins.

References:

WO2013/45431,2013,A1 Location in patent:Page/Page column 82