IR (neat): 2979, 1643, 1446, 1365, 1174, 1115 cm-1. HRMS (ESI) m/z calcd. For C20H21N2O4S (M+H)+, 385.1222, located 385.1215. 2-(Benzothiophen-2-yl)-1-morpholinoethan-1-one (5i)–General procedure A was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:three) offered the title compound as a light orange solid in 62 yield (81 mg). mp 11820 . 1H NMR (500 MHz, CDCl3): 7.79 (d, J = 7.8 Hz, 1H), 7.70 (d, J = 7.9 Hz, 1H), 7.33-7.29 (m, 3H), 3.98 (s, 2H), 3.68-3.67 (m, 4H), 3.59 (t, J = four.3 Hz, 2H), 3.54-3.53 (m, 2H). 13C NMR (125.eight MHz, CDCl3): 167.9, 139.7, 139.6, 137.three, 124.3, 124.0, 123.1, 122.six, 122.1, 66.6, 66.four, 46.six, 42.two, 35.7. IR (neat): 2920, 1644, 1436, 1229, 1113 cm-1. HRMS (ESI) m/z calcd. For C14H16NO2S (M+H)+, 262.0902, found 262.0898. 1-(Piperidin-1-yl)-2-(p-tolyl)ethan-1-one (5j).29–General process A was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:three) offered the title compound as a white strong in 86 yield (93 mg). Spectral data were in accordance with those published. mp 590 . 1H NMR (500 MHz, CDCl3): 7.11-7.ten (m, 4H), three.66 (s, 2H), three.54 (t, J = five.4 Hz, 2H), three.33 (t, J = 5.5 Hz, 2H), 2.29 (s, 3H), 1.57-1.55 (m, 2H), 1.50-1.49 (m, 2H), 1.32 (qt, J = five.two Hz, 2H). 13C NMR (125.8 MHz, CDCl3): 169.6, 136.3, 132.4, 129.five, 128.5, 47.four, 43.0, 41.0, 26.three, 25.6, 24.six, 21.two. N,N-Diethyl-2-(p-tolyl)acetamide (5k).30–General process A was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:three) offered the title compound as a white solid in 72 yield (74 mg). Spectral information have been in accordance with those published. mp 10305 . 1H NMR (500 MHz, CDCl3): 7.17-7.12 (m, 4H), 3.67 (s, 2H), 3.41 (q, J = 6.8 Hz, 2H), 3.31 (q, J = 7.1 Hz, 2H), two.34 (s, 3H), 1.12 (dt, J = 14.8, 7.three Hz, 6H). 13C NMR (125.eight MHz, CDCl3): 170.four, 136.3, 132.five, 129.4, 128.six, 42.four, 40.6, 40.2, 21.2, 14.3, 13.1. Basic procedure B for cross-coupling of (hetero)aryltrifluoroborates with secondary 2chloroacetamides An oven-dried Biotage ten mL microwave vial equipped using a magnetic stirbar was charged using the (hetero)aryl trifluoroborate (0.525 mmol, 1.05 equiv), Cs2CO3 (1.5 mmol, 3 equiv), XPhos-Pd-G2 (3.Physcion Epigenetic Reader Domain 93 mg, five.0 mol, 1 mol ), and Cu2O (three.6 mg, 25 mol, five mol ). A disposable Teflon septum cap was utilized to seal the vial, which was evacuated and purged with Ar three instances. THF (1.6 mL), H2O (0.four mL), as well as the electrophile (0.five mmol, 1 equiv) have been added through syringe with stirring beneath Ar. In cases exactly where the electrophile was a solid, it was added in addition to the solid supplies prior to sealing the vial.N-trans-Caffeoyltyramine Formula The soln was heated atNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptJ Org Chem.PMID:32472497 Author manuscript; obtainable in PMC 2014 April 19.Molander et al.Pageovernight. Following cooling to rt, the mixture was extracted with EtOAc (three mL), plus the combined organic layers have been dried (Na2SO4). The crude products had been purified by flash column chromatography, eluting using a gradient of EtOAc in hexanes. N-Benzyl-2-(quinolin-6-yl)acetamide (6a)–General procedure B was employed. Column chromatography (hexanes/EtOAc = 9:1 to 1:4) provided the title compound as a light orange strong in 55 yield (76 mg). mp 13537 . 1H NMR (500 MHz, CDCl3): 8.89-8.88 (m, 1H), eight.10-8.06 (m, 2H), 7.75 (s, 1H), 7.62 (d, J = eight.6 Hz, 1H), 7.41 (ddd, J = eight.two, 4.two, 1.0 Hz 1H), 7.29-7.26 (m, 3H), 7.22 (t, J = five.7 Hz, 2H), 5.84 (br s, 1H), four.43 (d, J = five.eight Hz, 2H), 3.79 (s, 2H). 13C NMR (125.8 MHz, CDCl3): 170.four, 150.six, 138.1, 136.5, 136.0, 133.4, 131.1, 130.