Ethanamine, 2,2,2-trifluoro- → 2-(4-isopropylphenyl)-N-((1R)-1-{5-[(2,2,2-trifluoroethyl)amino]pyridin-2-yl}ethyl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a 10.0 ml microwave reaction tube was added N-[(1R)-1-(5-bromopyridin-2-yl)ethyl]-2-(4-isopropylphenyl)acetamide (0.100 g, 0.277 mmol), trifluoroethylamine (0.025 ml, 0.332 mmol), NaOtBu (0.042 g, 0.441 mmol), (+/−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.018 g, 0.029 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.013 g, 0.015 mmol) and 2.5 ml of anhydrous toluene. N2 was bubbled through the mixture while stirring for 5 minutes. Then it was heated at 120° C. for 15 minutes in a microwave reaction chamber. Cooled to room temperature, filtered and concentrated. The residue was purified using reverse phase HPLC to afford 2-(4-isopropylphenyl)-N-((1R)-1-{5-[(2,2,2-trifluoroethyl)amino]pyridin-2-yl}ethyl)acetamide as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.291 (d, J=6.84 Hz, 1H); 8.174 (s, 1H); 7.516 (d, J=8.79 Hz, 1H); 7.357 (d, J=8.79 Hz, 1H); 7.167 (d, J=8.30 Hz, 2H); 7.141 (d, J=8.30 Hz, 2H); 5.823 (br s, 1H); 5.106 (dq, J=7.32 Hz, 1H); 3.692 (br d, J=7.57 Hz, 2H); 3.543 (d, J=14.90 Hz, 1H); 3.501 (d, J=15.14 Hz, 1H); 2.852 (sept, J=6.83 Hz, 1H); 1.563 (d, J=7.08 Hz, 3H); 1.199 (d, J=7.08 Hz, 6H); MS (Electrospray): m/z 380.1 (M+H).

Provenance & Evidence