Ne (5j).29General process A was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:3) offered the title compound as a white strong in 86 yield (93 mg). Spectral data have been in accordance with those published. mp 590 . 1H NMR (500 MHz, CDCl3): 7.117.10 (m, 4H), 3.66 (s, 2H), three.54 (t, J = 5.4 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.two Hz, 2H). 13C NMR (125.8 MHz, CDCl3): 169.six, 136.three, 132.4, 129.five, 128.5, 47.4, 43.0, 41.0, 26.three, 25.6, 24.six, 21.two. N,NDiethyl2(ptolyl)acetamide (5k).30General procedure A was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:3) supplied the title compound as a white solid in 72 yield (74 mg). Spectral information were in accordance with these published. mp 10305 . 1H NMR (500 MHz, CDCl3): 7.177.12 (m, 4H), three.67 (s, 2H), three.41 (q, J = 6.eight Hz, 2H), 3.31 (q, J = 7.1 Hz, 2H), two.34 (s, 3H), 1.12 (dt, J = 14.eight, 7.three Hz, 6H). 13C NMR (125.8 MHz, CDCl3): 170.4, 136.3, 132.five, 129.4, 128.6, 42.four, 40.6, 40.two, 21.2, 14.3, 13.1. Common process B for crosscoupling of (hetero)aryltrifluoroborates with secondary 2chloroacetamides An ovendried Biotage ten mL microwave vial equipped having a magnetic stirbar was charged together with the (hetero)aryl trifluoroborate (0.525 mmol, 1.05 equiv), Cs2CO3 (1.five mmol, three equiv), XPhosPdG2 (three.93 mg, five.0 mol, 1 mol ), and Cu2O (three.6 mg, 25 mol, 5 mol ). A disposable Teflon septum cap was made use of to seal the vial, which was evacuated and purged with Ar three times. THF (1.six mL), H2O (0.4 mL), as well as the electrophile (0.5 mmol, 1 equiv) have been added via syringe with stirring below Ar. In cases exactly where the electrophile was a solid, it was added in conjunction with the strong components before sealing the vial. The soln was heated atNIHPA Author Manuscript NIHPA Author Manuscript NIHPA Author ManuscriptJ Org Chem. Author manuscript; available in PMC 2014 April 19.Molander et al.Pageovernight. After cooling to rt, the mixture was extracted with EtOAc (3 mL), and the combined organic layers were dried (Na2SO4). The crude merchandise had 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) provided the title compound as a light orange solid in 55 yield (76 mg). mp 13537 . 1H NMR (500 MHz, CDCl3): 8.898.88 (m, 1H), 8.108.06 (m, 2H), 7.75 (s, 1H), 7.62 (d, J = eight.six Hz, 1H), 7.41 (ddd, J = 8.2, 4.2, 1.0 Hz 1H), 7.297.26 (m, 3H), 7.22 (t, J = five.7 Hz, 2H), 5.84 (br s, 1H), four.43 (d, J = 5.8 Hz, 2H), three.79 (s, 2H). 13C NMR (125.eight MHz, CDCl3): 170.4, 150.six, 138.1, 136.5, 136.0, 133.4, 131.1, 130.three, 129.three, 128.8, 128.4, 128.2, 127.eight, 127.7, 126.Buy2-(1H-Pyrazol-3-yl)propan-2-ol 2, 121.Tetrahydro-2H-pyran-4-carbaldehyde Purity 7, 43.PMID:33484385 9, 43.eight. IR (neat): 3229, 2361, 1628, 1554, 1328 cm1. HRMS (ESI) m/z calcd. For C18H17N2O (MH) 277.1341, discovered 277.1339. NBenzyl2(ptolyl)acetamide (6b).31General process B was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:four) offered the title compound as a white strong in 75 yield (90 mg). Spectral information were 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.two Hz, 2H), 7.18 (s, 4H), 5.67 (br s, 1H), four.41 (d, J = five.6 Hz, 2H), 3.60 (s, 2H), two.33 (s, 3H). 13C NMR (125.eight MHz, CDCl3): 171.three, 138.four, 137.two, 131.eight, 129.9, 129.five, 128.eight, 127.6, 127.5, 43.7, 43.six, 21.2. NCyclopropyl2(ptolyl)acetamide (6c)Basic procedure B was employed. Column chromatography (.