Ne (5j).29General process A was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:3) provided the title compound as a white solid in 86 yield (93 mg). Spectral information had been in accordance with those published. mp 590 . 1H NMR (500 MHz, CDCl3): 7.117.10 (m, 4H), three.66 (s, 2H), three.54 (t, J = five.4 Hz, 2H), three.33 (t, J = five.five Hz, 2H), 2.29 (s, 3H), 1.571.55 (m, 2H), 1.501.49 (m, 2H), 1.32 (qt, J = five.2 Hz, 2H). 13C NMR (125.eight MHz, CDCl3): 169.6, 136.three, 132.four, 129.5, 128.5, 47.four, 43.0, 41.0, 26.3, 25.6, 24.six, 21.two. N,NDiethyl2(ptolyl)acetamide (5k).30General process A was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:three) supplied the title compound as a white strong in 72 yield (74 mg). Spectral information were in accordance with those published. mp 10305 . 1H NMR (500 MHz, CDCl3): 7.177.12 (m, 4H), three.67 (s, 2H), 3.41 (q, J = 6.eight Hz, 2H), 3.31 (q, J = 7.1 Hz, 2H), 2.34 (s, 3H), 1.12 (dt, J = 14.8, 7.three Hz, 6H). 13C NMR (125.8 MHz, CDCl3): 170.four, 136.three, 132.5, 129.four, 128.6, 42.four, 40.six, 40.two, 21.two, 14.three, 13.1. General process B for crosscoupling of (hetero)aryltrifluoroborates with secondary 2chloroacetamides An ovendried Biotage ten mL microwave vial equipped with a magnetic stirbar was charged with all the (hetero)aryl trifluoroborate (0.525 mmol, 1.05 equiv), Cs2CO3 (1.5 mmol, 3 equiv), XPhosPdG2 (3.93 mg, 5.0 mol, 1 mol ), and Cu2O (3.6 mg, 25 mol, five mol ). A disposable Teflon septum cap was utilized to seal the vial, which was evacuated and purged with Ar 3 occasions. THF (1.6 mL), H2O (0.4 mL), and the electrophile (0.five mmol, 1 equiv) had been added by means of syringe with stirring below Ar. In circumstances where the electrophile was a solid, it was added together with the strong components just before sealing the vial. The soln was heated atNIHPA Author Manuscript NIHPA Author Manuscript NIHPA Author ManuscriptJ Org Chem. Author manuscript; obtainable in PMC 2014 April 19.Molander et al.Pageovernight. Following cooling to rt, the mixture was extracted with EtOAc (3 mL), plus the combined organic layers have been dried (Na2SO4). The crude solutions have been purified by flash column chromatography, eluting with a gradient of EtOAc in hexanes. NBenzyl2(quinolin6yl)acetamide (6a)General process B was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:four) supplied the title compound as a light orange solid in 55 yield (76 mg). mp 13537 . 1H NMR (500 MHz, CDCl3): eight.898.88 (m, 1H), 8.108.06 (m, 2H), 7.75 (s, 1H), 7.62 (d, J = 8.6 Hz, 1H), 7.41 (ddd, J = 8.two, four.3-Bromo-4-methylaniline Chemical name 2, 1.220497-67-6 Formula 0 Hz 1H), 7.PMID:31085260 297.26 (m, 3H), 7.22 (t, J = five.7 Hz, 2H), 5.84 (br s, 1H), 4.43 (d, J = five.eight Hz, 2H), three.79 (s, 2H). 13C NMR (125.eight MHz, CDCl3): 170.4, 150.6, 138.1, 136.five, 136.0, 133.4, 131.1, 130.three, 129.three, 128.8, 128.4, 128.two, 127.eight, 127.7, 126.two, 121.7, 43.9, 43.8. IR (neat): 3229, 2361, 1628, 1554, 1328 cm1. HRMS (ESI) m/z calcd. For C18H17N2O (MH) 277.1341, located 277.1339. NBenzyl2(ptolyl)acetamide (6b).31General procedure B was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:4) offered the title compound as a white solid in 75 yield (90 mg). Spectral data have been in accordance with those published. mp 13435 (lit. 136). 1H NMR (500 MHz, CDCl3): 7.33 (t, J = 7.2 Hz, 2H), 7.277.26 (m, 1H), 7.21 (d, J = 7.2 Hz, 2H), 7.18 (s, 4H), five.67 (br s, 1H), 4.41 (d, J = five.six Hz, 2H), 3.60 (s, 2H), two.33 (s, 3H). 13C NMR (125.8 MHz, CDCl3): 171.three, 138.four, 137.two, 131.8, 129.9, 129.5, 128.eight, 127.6, 127.5, 43.7, 43.6, 21.2. NCyclopropyl2(ptolyl)acetamide (6c)Common procedure B was employed. Column chromatography (.