Hydrochloric Acid → HCID 67125611, compound

Participants

Reaction Steps

A solution of 3-(2-cyanopropan-2-yl)-N-(3-iodo-4-methylphenyl)benzamide 111 (1.546 mmol, 625 mg), 1-ethoxyvinyltri-n-butyltin (4.64 mmol, 1.567 mL) and bis(triphenylphosphine)palladium(II) chloride (0.155 mmol, 109 mg) in toluene (5 mL) was stirred at 100° C. for 2 h. Cooled down to room temperature, 4N HCl in dioxane (1 mL) was added and stirred for 1 h. Diluted with ethyl acetate, filtrated and evaporated. Purification by chromatography (0-5% ethyl acetate in CH2Cl2) gave N-(3-acetyl-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 112 (364 mg, 73.5%). NMR (400 MHz, CDCl3) 1.79 (s, 6H), 2.52 (s, 3H), 2.62 (s, 3H), 7.26 (d, J=8.2 Hz, 1H), 7.55 (m, 2H), 7.72 (d, J=7.8 Hz, 1H), 7.81 (d, J=7.4 Hz, 1H), 7.91 (br s, 1H), 8.00 (t, J=1.9 Hz, 1H), 8.15 (d, J=2.3 Hz, 1H).

Provenance & Evidence