Hz, CDCl3) 7.80 (d, J = eight.0 Hz, 1H), 7.52 (d, J = 7.9 Hz, 2H), 7.30-6.97 (m, 4H), 5.46 (s, 1H), three.95 (s, 3H), three.92-3.87 (m, 1H), 3.62-3.59 (m, 1H) 2.62 (s, 3H), 2.05-1.97 (m, 1H), 1.87-1.86 (m, 2H), 1.72-1.65 (m, 2H), 1.60-1.58 (m, 1H); 13C NMR (125 MHz, CDCl3) 199.two, 159.five, 157.five, 146.7, 133.five, 131.2, 128.4, 126.three,dx.doi.org/10.1021/jm401916j | J. Med. Chem. 2014, 57, 2643-Journal of Medicinal Chemistry119.1, 116.9, 110.0, 96.4, 62.1, 55.six, 32.0, 30.four, 25.three, 18.8; IR (neat cm-1) 2940, 2872, 2847, 1656, 1598, 1358, 1280, 1177, 1019, 813, 518; HRMS (DART, M+ + H) m/z 327.1612 (calculated for C20H23O4, 327.1596). 1-(3-Methoxy-4-methyl-biphenyl-4-yl)-ethanone (12). In accordance with the common Suzuki coupling procedure, ketone 7 (0.465 g, two.03 mmol), 4-tolylboronic acid (0.551 g, 4.06 mmol), Cs2CO3 (1.98 g, 6.09 mmol), Pd(PPh3)2Cl2 (0.142 g, 0.20 mmol, ten Pd), and anhydrous dioxane (six mL) have been heated at 80 for 5 h. Following the common workup and flash chromatography (SiO2, 20 g, five EtOAc/ hexanes), biaryl ketone 12 was obtained as a white solid (0.375 g, 77 ): TLC Rf = 0.57 (25 EtOAc/hexanes); mp 84.2-86.1 ; 1H NMR (500 MHz, CDCl3) 7.87 (d, J = eight.0 Hz, 1H), 7.55 (d, J = 7.6 Hz, 2H), 7.31 (d, J = 7.six Hz, 2H), 7.24 (d, J = eight.0 Hz, 1H), 7.18 (s, 1H), four.01 (s, 3H), two.69 (s, 3H), 2.45 (s, 3H); 13C NMR (125 MHz, CDCl3) 198.Anti-Mouse CD44 Antibody 9, 159.four, 146.8, 138.1, 137.1, 130.9, 129.six, 126.9, 126.4, 119.1, 110.0, 55.four, 31.eight, 21.1; IR (neat cm-1) 3028, 2949, 2921, 1657, 1551, 1223, 1013, 808, 510; HRMS (DART, M+ + H) m/z 241.1251 (calculated for C16H17O2, 241.1229). 4-Acetyl-3-methoxy-biphenyl-4-carbonitrile (13). As outlined by the common Suzuki coupling process, ketone 7 (0.500 g, two.18 mmol), 4-cyanophenylboronic acid (0.640 g, 4.36 mmol), Cs2CO3 (2.14 g, 6.55 mmol), Pd(PPh3)2Cl2 (0.154 g, 0.22 mmol, 10 Pd), and anhydrous dioxane (6 mL) were heated at 80 for 14 h (overnight). Following the basic workup and flash chromatography (SiO2, 20 g, 10 EtOAc/hexanes), biaryl ketone 13 was obtained as a white solid (0.470 g, 86 ): TLC Rf = 0.4 (25 EtOAc/hexanes); mp 125-127.two ; 1H NMR (500 MHz, CDCl3) 7.84 (d, J = eight.0 Hz, 1H), 7.76- 7.73 (m, 2H), 7.71-7.68 (m, 2H), 7.20 (dd, J = eight.0, 1.6 Hz, 1H), 7.13 (d, J = 1.five Hz, 1H), 4.00 (s, 3H), two.64 (s, 3H); 13C NMR (125 MHz, CDCl3) 199.Mogamulizumab two, 159.PMID:23522542 five, 144.8, 144.7, 132.9, 131.5, 128.2, 128.1, 119.8, 118.eight, 112.1, 110.7, 55.9, 32.0; IR (neat cm-1) 3073, 3046, 2923, 2225, 1652, 1601, 1468, 1225, 1023, 812,543; HRMS (DART, M+ + H) m/z 252.1032 (calculated for C16H14NO2, 252.1024). 4-Acetyl-3-methoxy-biphenyl-4-carboxylic Acid Methyl Ester (14). In accordance with the general Suzuki coupling process, ketone 7 (0.506 g, two.21 mmol), 4-(methoxycarbonyl)phenylboronic acid (0.795 g, four.42 mmol), Cs2CO3 (two.16 g, six.63 mmol), Pd(PPh3)2Cl2 (0.155 g, 0.22 mmol, 10 Pd), and anhydrous dioxane (6 mL) have been heated at 80 for 14 h (overnight). Following the general workup and flash chromatography (SiO2, 20 g, 15 EtOAc/hexanes), biaryl ketone 14 was obtained as a white solid (0.490 g, 78 ): TLC Rf = 0.four (25 EtOAc/hexanes); mp 140.4-142.six ; 1H NMR (500 MHz, CDCl3) 8.09 (d, J = eight.0 Hz, 2H), 7.81 (d, J = 8.0 Hz, 1H), 7.63 (d, J = eight.0 Hz, 2H), 7.20 (d, J = eight.0 Hz, 1H), 7.14 (s, 1H), three.97 (s, 3H), 3.91 (s, 3H), 2.62 (s, 3H); 13C NMR (125 MHz, CDCl3) 199.3, 166.9, 159.5, 145.6, 144.7, 131.three, 130.3, 129.9, 127.5, 127.four, 119.eight, 110.7, 55.eight, 52.4, 32.1; IR (neat cm-1) 2997, 2955, 2929, 2845, 2162, 1714, 1657, 1604, 1554, 1280, 1247, 831, 768. HRMS.
