Yellow oil in 80 yield (66 mg). Spectral data have been in accordance with those published. 1H NMR (500 MHz, CDCl3): 7.14-7.12 (m, 4H), 3.66 (s, 3H), three.57 (s, 2H), two.31 (s, 2H). 13C NMR (125.8 MHz, CDCl3): 172.four, 136.9, 131.1, 129.five, 129.three, 52.two, 40.9, 21.two. tert-Butyl 2-(Quinolin-6-yl)acetate (4a).20–General process A was employed. Column chromatography (hexanes/EtOAc = 9:1 to 3:1) supplied the title compound an orange-brown oil in 92 yield (112 mg). Spectral data had been in accordance with these published. 1H NMR (500 MHz, CDCl3): eight.89-8.87 (m, 1H), 8.16 (dd, J = eight.1, 4.6 Hz, 1H), 8.10-8.08 (m, 1H), 7.69 (s, 1H), 7.68-7.66 (m, 1H), 7.42-7.40 (m, 1H), three.70 (s, 2H), 1.43 (s, 9H). 13C NMR (125.eight MHz, CDCl3): 170.7, 150.three, 147.6, 135.9, 133.three, 131.3, 129.6, 128.3, 127.8, 121.4, 81.three, 42.7, 28.2. tert-Butyl 2-(Isoquinolin-5-yl)acetate (4b)–General procedure A was employed. Column chromatography (hexanes/EtOAc = 9:1 to 3:1) offered the title compound as an orange-brown oil in 94 yield (114 mg). 1H NMR (500 MHz, CDCl3): 9.24 (s, 1H), 8.Naringin Cytochrome P450 60 (t, J = five.0 Hz, 1H), 7.95 (d, J = eight.0 Hz, 1H), 7.77-7.76 (m, 1H), 7.65 (d, J = six.9 Hz, 1H), 7.58-7.56 (m, 1H), three.94 (s, 2H), 1.39 (s, 9H). 13C NMR (125.eight MHz, CDCl3): 170.4, 153.2, 143.3, 135.0, 132.1, 130.eight, 129.1, 127.four, 127.1, 117.1, 81.six, 39.eight, 28.1. IR (neat): 2977, 1728, 1367, 1253, 1145 cm-1. HRMS (ESI) m/z calcd. For C15H18NO2 (M+H)+ 244.1338, found 244.1338. tert-Butyl 2-(Pyridin-3-yl)acetate (4c).25–General process A was employed, with all the only modification getting that two mol of XPhos-Pd-G2 was employed. Column chromatography (hexanes/EtOAc = 9:1 to 3:1) offered the title compound as a brown oil inJ Org Chem. Author manuscript; available in PMC 2014 April 19.Molander et al.Page57 yield (55 mg). Spectral data had been in accordance with these published. 1H NMR (500 MHz, CDCl3): 8.51-8.50 (m, 2H), 7.64-7.62 (m, 1H), 7.26-7.24 (m, 1H), 3.53 (s, 2H), 1.44 (s, 9H). 13C NMR (125.eight MHz, CDCl3): 170.1, 150.five, 148.5, 136.9, 130.5, 123.five, 81.six, 39.Icariin Metabolic Enzyme/Protease,Vitamin D Related/Nuclear Receptor,Cell Cycle/DNA Damage,Autophagy 9, 28.PMID:23715856 1. tert-Butyl 2-(two,4-Dimethoxypyrimidin-5-yl)acetate (4d)–General procedure A was employed. Column chromatography (hexanes/EtOAc = 9:1 to 3:1) offered the title compound as a yellow solid in 93 yield (118 mg). mp 402 . 1H NMR (500 MHz, CDCl3): 8.02 (s, 1H), 3.96 (s, 6H), three.36 (s, 2H), 1.41 (s, 9H). 13C NMR (125.8 MHz, CDCl3): 169.9, 169.5, 164.8, 158.0, 109.three, 81.two, 54.eight, 54.0, 33.5, 28.1. IR (neat): 2985, 1730, 1569, 1470, 1380, 1227, 1147 cm-1. HRMS (ESI) m/z calcd. For C12H19N2O4 (M +H)+ 255.1345, identified 255.1347. tert-Butyl 2-(Isoquinolin-4-yl)acetate (4e)–General process A was employed, together with the only modification becoming that two mol of XPhos-Pd-G2 was applied. Column chromatography (hexanes/EtOAc = 9:1 to three:1) provided the title compound as an orangebrown oil in 80 yield (97 mg). 1H NMR (500 MHz, CDCl3): 9.19-9.18 (m, 1H), eight.43-8.42 (m, 1H), eight.00-7.97 (m, 2H), 7.75-7.72 (m, 1H), 7.62-7.61 (m, 1H), three.93 (s, 2H), 1.40 (s, 9H). 13C NMR (125.eight MHz, CDCl3): 170.1, 151.9, 147.3, 135.eight, 129.three, 129.three, 128.0, 127.7, 126.9, 81.six, 40.1, 28.1. IR (neat): 2977, 1728, 1367, 1141 cm-1. HRMS (ESI) m/z calcd. For C15H18NO2 (M+H)+ 244.1338, located 244.1336. tert-Butyl 2-(Pyridin-4-yl)acetate (4f).26–General procedure A was employed. Column chromatography (hexanes/EtOAc = 9:1 to three:1) supplied the title compound as a brown oil in 40 yield (39 mg). Spectral data were in accordance with those published. 1H NMR (500 MHz, CDCl3): 8.56-8.54 (m, 2H), 7.21-7.20 (m, two.