2-ethyl-N-(2-methylpropyl)aniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-ethyl-N-isobutylaniline (83 mg, 0.468 mmol) was dissolved in pyridine (3 mL) add 4-vinylbenzene-1-sulfonyl chloride (114 mg, 0.562 mmol) added. Reaction stirred for over the weekend. Ethyl acetate (10 mL) was added to the solution and the organic phase was washed with water (10 mL), sodium hydroxide solution (2M, 2×10 mL) and brine (10 mL), then dried and concentrated under vacuum to provide the product, 129 mg. LCMS [LCMS1] Rt 1.43 min, m/z (ES+) 344 (M+H). added Reaction the organic phase was washed with water (10 mL), sodium hydroxide solution (2M, 2×10 mL) and brine (10 mL) dried concentrated under vacuum to provide the product, 129 mg

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-ethylaniline (0.102 mL, 0.825 mmol), 2-methylpropan-1-ol (0.305 mL, 3.30 mmol), potassium iodide (274 mg, 1.650 mmol) and [Cp*IrCl2]2 (10.52 mg, 0.013 mmol) were added to a microwave vial with water (1.5 mL). This was heated, by microwaves, for 90 minutes at 150° C. Dichloromethane (10 mL) and water (10 mL) were added and the phases separated using a hydrophobic frit. The aqueous layer was further extracted with dichloromethane (15 mL). The combined organic layers were concentrated under vacuum and purified by silica (Si) chromatography (0-50% dichloromethane-cyclohexane gradient). The relevant fractions were concentrated to provide the product as a clear oil, 0.83 mg. LCMS [LCMS1] Rt 1.26 min, m/z (ES+) 178 (M+H). the phases separated The aqueous layer was further extracted with dichloromethane (15 mL) The combined organic layers were concentrated under vacuum purified by silica (Si) chromatography (0-50% dichloromethane-cyclohexane gradient) The relevant fractions were concentrated