Triethylamine → HCID 25224408, compound

Participants

Reaction Steps

A solution of palladium (II) acetate (0.065 g, 0.29 mmol), the product from Example 2F (1.03 g, 2.90 mmol), triethylamine (0.293 mg, 2.90 mmol), 2-dicyclohexylphosphine-2′-(N,N-dimethylamino)biphenyl (0.228 g, 0.579 mmol) and p-trifluoromethylaniline (0.933 g, 5.79 mmol) in N,N-dimethylformamide (20 mL) was placed under 1 atmosphere of carbon monoxide and stirred at room temperature for 2 hours. The reaction mixture was concentrated to approximately, poured into of ethyl acetate, washed with saturated sodium bicarbonate, dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography (gradient elution from 0% to 20% ethyl acetate-[50% CH2Cl2-hexane] to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.19 (dd, 1H, J=4.7, 1.7 Hz), 7.71 (d, 2H, J=8.5 Hz), 7.62 (dd, 1H, J=7.8, 1.7 Hz), 7.60 (d, 2H, J=8.5 Hz), 6.86 (dd, 1H, J=7.8, 4.7 Hz), 6.61 (dd, 1H, J=3.1, 3.1 Hz), 4.19-3.96 (m, 2H), 3.63 (dd, 1H, J=12.5, 4.1 Hz), 3.35 (dd, 1H, J=12.5, 4.1 Hz), 3.14-3.02 (m, 1H), 1.29 (d, 3H, J=7.1 Hz); MS (DCI/NH3) m/e 396 (M+H)+; [α]23D +37.2° (c 1.0, CH3OH).

Provenance & Evidence