Produce (%) = 77. (bs, 1H), 9.19 (bs, 1H), 7.63 (s, 1H), 7.50 (d, (6). Produce (%) = 77. 1H NMR (500?MHz, DMSO): 12.35 (s, 1H), 9.69 (bs, 1H), 9.29 (bs, 1H), Klf2 8.37 (s, 1H), 8.07 (d, (7). Produce (%) = 80. 1H NMR (500?MHz, DMSO): 12.02 (s, 1H), 9.52 (bs, 1H), 9.23 (bs, 1H), 8.43 (d, (8). Produce (%) = 87. 1H NMR (500?MHz, DMSO): 11.56 (s, 1H), 9.45 (bs, 1H), 9.27 (bs, 1H), 8.35 (s, 1H), 8.03 (d, J?=?8.0?Hz, 1H), 7.67(d, J?=?8.0?Hz, 1H), 7.13 (s, 1H), 6.83 (d, J?=?7.0?Hz, 1H), 6.78 (d, J?=?7.0?Hz, 1H) ppm. 13?C NMR (500?MHz, DMSO): 162.00, 160.54,154.27, 147.12, 146.04, 145.76,138.59, 134.73, 127.17, 122.22, 119.19, 116.15, 110.90?ppm. HRMS determined for C14H9IN2O3 379.97, found 379.97. (9). Produce (%) = 79. 1H NMR (500?MHz, DMSO): 12.11 (s, 1H), 9.56 (bs, 1H), 9.33 (bs, 1H), 8.15 (s, 1H), 7.98 (d, (10). Produce (%) = 90. 1H NMR (500?MHz, DMSO): 12.34 (s, 1H), 9.47 (bs, 1H), 9.38 (bs, 1H), 8.02(s, 1H), 7.78 (d, (11). Produce (%) = 87. 1H NMR (500?MHz, DMSO): 12.45 (s, 1H), 9.82 (bs, 1H), 9.42 (bs, 1H), 8.20 (d, (12). Produce (%) = 93. 1H NMR (500?MHz, DMSO): 12.46 (s, 1H), 9.76 (bs, 1H), 9.39 (bs, 1H), 7.88 (d, (13). Produce (%) = 84. 1H NMR (500?MHz, DMSO): 12.66 (s, 1H), 9.49 (bs, 1H), 8.78 (bs, 1H), 8.42 (d, (15). Produce (%) = 91. 1H NMR (500?MHz, DMSO): 12.73 (s, 1H), 9.65 (bs, 1H), 9.31 (bs, 1H), 8.08 (d, (16). Produce (%) = 81. 1H NMR (500?MHz, DMSO): 12.45 (s, 1H), 9.57 (bs, 1H), 9.01 (bs, 1H), 8.77 (d, (17). Produce (%) = 93. 1H NMR (500?MHz, DMSO): 12.20 (s, 1H), 9.63 (bs, 1H), 9.28 (bs, 1H), 8.11 (d, J?=?9.0?Hz, 1H), 7.79 (d, J?=?9.0?Hz, 1H), 7.67(s, 1H), 7.65 (t, J?=?9.0?Hz, 2H), 7.43 (d, J?=?8.0?Hz, 1H), 6.85 (d, J?=?9.0?Hz, 1H), ppm. 13?C NMR (500?MHz, DMSO): 161.00, 159.17, 157.12, 149.72, 145.43, 138.12, 134.96, 133.31, 122.33, 120.00, 116.42, 114.15?ppm. HRMS determined for C14H10N2O3 254.07 found 254.06. (18). Produce (%) = 89. 1H NMR (500?MHz, DMSO): 13.12 (bs, 1H), 12.15 (s, 1H), 11.06 (bs, 1H), 8.22 (d, (19). Produce (%) = 83. 1H NMR (500?MHz, DMSO): 12.34 (s, 1H), 10.03 (bs, 1H), 8.03 (d, (20). Produce (%) = 82. 1H NMR (500?MHz, DMSO): 11.98 (s, 1H) 8.25 (d, (21). Produce (%) = 92. 1H NMR (500?MHz, DMSO): 12.21 (s, 1H), 8.13 (d, (14), (22), and (23) (14). 2-amino-5-chlorobenzamide (0.7?mmol) and 3,4-dihydroxybenzaldehyde (0.91?mmol) were dissolved in an assortment of dichloromethane (10?ml) and acetonitrile (7?ml) and refluxed for 40?h. After conclusion, the solvent was eliminated under vacuum. The solid residue was treated with drinking water, filtered and washed once again with water to provide compound 14 like a pale yellowish crystal. Produce (%) = 82. 1H NMR (500?MHz, DMSO): 9.42 (s, 1H), 8.47 (bs, 1H), 8.38 (bs, 1H), 7.99 (s, 1H), 7.85 (d, (22). To an assortment of (3,4-dimethoxyphenyl)boronic acidity (3.29?mmol), K2CO3 (3.29?mmol), and Pd(OAc)2 (0.027?mmol) in ethanol (9?ml) and drinking water (3?ml) was slowly added 2-bromoquinoline (2.74?mmol). The blend was stirred at space temp for 18?h. Towards the ensuing blend was added drinking water (50?ml), and extracted with dichloromethane then. The organic stage was separated, dried out over Mg2Thus4 and focused under decreased pressure to provide a good residue that was purified by adobe flash chromatography (silica gel and hexane/acetone 3/1). The genuine 2C(3,4-dimethoxyphenyl)quinoline was acquired as light gray solid and useful for the next response. Produce (%) = 92. 1H NMR (500?MHz, DMSO): 8.76 (d, 4-(naphthalen-2-yl)benzene-1,2-diol (23). To an assortment of 2-naphtylboronic acidity (5.81?mmol), K2CO3 (5.81?mmol), and Pd(OAc)2 (0.048?mmol) in ethanol (15?ml) and drinking water (5?ml) was slowly added 4-bromo-1,2-dimethoxybenzene (4.84?mmol). The blend was stirred at space temp for 18?h. Towards the ensuing blend was added drinking water (80?ml), and extracted with dichloromethane. The organic stage was separated, dried out over Mg2Thus4 and focused under decreased pressure to provide a.Produce (%) = 74. (bs, 1H), 9.29 (bs, L-655708 1H), 7.91 (s, 1H), 7.67(s, 1H), 7.61 (d, (3). Produce (%) = 68. 1H NMR (500?MHz, DMSO): 12.06 (s, 1H), 9.11 (bs, 1H), 8.48 (bs, 1H), 7.98 (d, (4). Produce (%) = 73. 1H NMR (500?MHz, DMSO): 12.16 (s, 1H), 9.56 (bs, 1H), 9.23 (bs, 1H), 7.65 (s, 1H), 7.61 (d, (5). Produce (%) = 74. 1H NMR (500?MHz, DMSO): 12.07 (s, 1H), 9.60 (bs, 1H), 9.19 (bs, 1H), 7.63 (s, 1H), 7.50 (d, (6). Produce (%) = 77. 1H NMR (500?MHz, DMSO): 12.35 (s, 1H), 9.69 (bs, 1H), 9.29 (bs, 1H), 8.37 (s, 1H), 8.07 (d, (7). Produce (%) = 80. 1H NMR (500?MHz, DMSO): 12.02 (s, 1H), 9.52 (bs, 1H), 9.23 (bs, 1H), 8.43 (d, (8). Produce (%) = 87. 1H NMR (500?MHz, DMSO): 11.56 (s, 1H), 9.45 (bs, 1H), 9.27 (bs, 1H), 8.35 (s, 1H), 8.03 (d, J?=?8.0?Hz, 1H), 7.67(d, J?=?8.0?Hz, 1H), 7.13 (s, 1H), 6.83 (d, J?=?7.0?Hz, 1H), 6.78 (d, J?=?7.0?Hz, 1H) ppm. 13?C NMR (500?MHz, DMSO): 162.00, 160.54,154.27, 147.12, 146.04, 145.76,138.59, 134.73, 127.17, 122.22, 119.19, 116.15, 110.90?ppm. HRMS determined for C14H9IN2O3 379.97, found 379.97. (9). Produce (%) = 79. 1H NMR (500?MHz, DMSO): 12.11 (s, 1H), 9.56 (bs, 1H), 9.33 (bs, 1H), 8.15 (s, 1H), 7.98 (d, (10). Produce (%) = 90. 1H NMR (500?MHz, DMSO): 12.34 (s, 1H), 9.47 (bs, 1H), 9.38 (bs, 1H), 8.02(s, 1H), 7.78 (d, (11). Produce (%) = 87. 1H NMR (500?MHz, DMSO): 12.45 (s, 1H), 9.82 (bs, 1H), 9.42 (bs, 1H), 8.20 (d, (12). Produce (%) = 93. 1H NMR (500?MHz, DMSO): 12.46 (s, 1H), 9.76 (bs, 1H), 9.39 (bs, 1H), 7.88 (d, (13). Produce (%) = 84. 1H NMR (500?MHz, DMSO): 12.66 (s, 1H), 9.49 (bs, 1H), 8.78 (bs, 1H), 8.42 (d, (15). Produce (%) = 91. 1H NMR (500?MHz, DMSO): 12.73 (s, 1H), 9.65 (bs, 1H), 9.31 (bs, 1H), 8.08 (d, (16). Produce (%) = 81. 1H NMR (500?MHz, DMSO): 12.45 (s, 1H), 9.57 (bs, 1H), 9.01 (bs, 1H), 8.77 (d, (17). Produce (%) = 93. 1H NMR (500?MHz, DMSO): 12.20 (s, 1H), 9.63 (bs, 1H), 9.28 (bs, 1H), 8.11 (d, J?=?9.0?Hz, 1H), 7.79 (d, J?=?9.0?Hz, 1H), 7.67(s, 1H), 7.65 (t, J?=?9.0?Hz, 2H), 7.43 (d, J?=?8.0?Hz, 1H), 6.85 (d, J?=?9.0?Hz, 1H), ppm. 13?C NMR (500?MHz, DMSO): 161.00, 159.17, 157.12, 149.72, 145.43, 138.12, 134.96, 133.31, 122.33, 120.00, 116.42, 114.15?ppm. HRMS determined for C14H10N2O3 254.07 found 254.06. (18). Produce (%) = 89. 1H NMR (500?MHz, DMSO): 13.12 (bs, 1H), 12.15 (s, 1H), 11.06 (bs, 1H), 8.22 (d, (19). Produce (%) = 83. 1H NMR (500?MHz, DMSO): 12.34 (s, 1H), 10.03 (bs, 1H), 8.03 (d, (20). Produce (%) = 82. 1H NMR (500?MHz, DMSO): L-655708 11.98 (s, 1H) 8.25 (d, (21). Produce (%) = 92. 1H NMR (500?MHz, DMSO): 12.21 (s, 1H), 8.13 (d, (14), (22), and (23) (14). 2-amino-5-chlorobenzamide (0.7?mmol) and 3,4-dihydroxybenzaldehyde (0.91?mmol) were dissolved in an assortment of dichloromethane (10?ml) and acetonitrile (7?ml) and refluxed for 40?h. After conclusion, the solvent was eliminated under vacuum. The solid residue was treated with drinking water, filtered and washed once again with water to provide compound 14 like a pale yellowish crystal. Produce (%) = 82. 1H NMR (500?MHz, DMSO): 9.42 (s, 1H), 8.47 (bs, 1H), 8.38 (bs, 1H), 7.99 (s, 1H), 7.85 (d, (22). To an assortment of (3,4-dimethoxyphenyl)boronic acidity (3.29?mmol), K2CO3 (3.29?mmol), and Pd(OAc)2 (0.027?mmol) in ethanol (9?ml) and drinking water (3?ml) was slowly added 2-bromoquinoline (2.74?mmol). The blend was stirred at space temp for 18?h. Towards the ensuing blend was added drinking water (50?ml), and extracted with dichloromethane. The organic stage was separated, dried out over Mg2Thus4 and focused under decreased pressure to provide a good residue that was purified by adobe flash chromatography (silica gel and hexane/acetone 3/1). The genuine 2C(3,4-dimethoxyphenyl)quinoline was acquired as light gray solid and useful for the next response. Produce (%) = 92. 1H NMR (500?MHz, DMSO): 8.76 (d, 4-(naphthalen-2-yl)benzene-1,2-diol (23). To an assortment of 2-naphtylboronic acidity (5.81?mmol), K2CO3 (5.81?mmol), and Pd(OAc)2 (0.048?mmol) in ethanol (15?ml) and drinking water (5?ml) was slowly added 4-bromo-1,2-dimethoxybenzene (4.84?mmol). The blend was stirred at space temp for 18?h. To.Towards the resulting blend was added drinking water (80?ml), and extracted with dichloromethane. Produce (%) = 74. 1H NMR (500?MHz, DMSO): 12.07 (s, 1H), 9.60 (bs, 1H), 9.19 (bs, 1H), 7.63 (s, 1H), 7.50 (d, (6). Produce (%) = 77. 1H NMR (500?MHz, DMSO): 12.35 (s, 1H), 9.69 (bs, 1H), 9.29 (bs, 1H), 8.37 (s, 1H), 8.07 (d, (7). Produce (%) = 80. 1H NMR (500?MHz, DMSO): 12.02 (s, 1H), 9.52 (bs, 1H), 9.23 (bs, 1H), 8.43 (d, (8). Produce (%) = 87. 1H NMR (500?MHz, DMSO): 11.56 (s, 1H), 9.45 (bs, 1H), 9.27 (bs, 1H), 8.35 (s, 1H), 8.03 (d, J?=?8.0?Hz, 1H), 7.67(d, J?=?8.0?Hz, 1H), 7.13 (s, 1H), 6.83 (d, J?=?7.0?Hz, 1H), 6.78 (d, J?=?7.0?Hz, 1H) ppm. 13?C NMR (500?MHz, DMSO): 162.00, 160.54,154.27, 147.12, 146.04, 145.76,138.59, 134.73, 127.17, 122.22, 119.19, 116.15, 110.90?ppm. HRMS determined for C14H9IN2O3 379.97, found 379.97. (9). Produce (%) = 79. 1H NMR (500?MHz, DMSO): 12.11 (s, 1H), 9.56 (bs, 1H), 9.33 (bs, 1H), 8.15 (s, 1H), 7.98 (d, (10). Produce (%) = 90. 1H NMR (500?MHz, DMSO): 12.34 (s, 1H), 9.47 (bs, 1H), 9.38 (bs, 1H), 8.02(s, 1H), 7.78 (d, (11). Produce (%) = 87. 1H NMR (500?MHz, DMSO): 12.45 (s, 1H), 9.82 (bs, 1H), 9.42 (bs, 1H), 8.20 (d, (12). Produce (%) = 93. 1H NMR (500?MHz, DMSO): 12.46 (s, 1H), 9.76 (bs, 1H), 9.39 (bs, 1H), 7.88 (d, (13). Produce (%) = 84. 1H NMR (500?MHz, DMSO): 12.66 (s, 1H), 9.49 (bs, 1H), 8.78 (bs, 1H), 8.42 (d, (15). Produce (%) = 91. 1H NMR (500?MHz, DMSO): 12.73 (s, 1H), 9.65 (bs, 1H), 9.31 (bs, 1H), 8.08 (d, (16). Produce (%) = 81. 1H NMR (500?MHz, DMSO): 12.45 (s, 1H), 9.57 (bs, 1H), 9.01 (bs, 1H), 8.77 (d, (17). Produce (%) = 93. 1H NMR (500?MHz, DMSO): 12.20 (s, 1H), 9.63 (bs, 1H), 9.28 (bs, 1H), 8.11 (d, J?=?9.0?Hz, 1H), 7.79 (d, J?=?9.0?Hz, 1H), 7.67(s, 1H), 7.65 (t, J?=?9.0?Hz, 2H), 7.43 (d, J?=?8.0?Hz, 1H), 6.85 (d, J?=?9.0?Hz, 1H), ppm. 13?C NMR (500?MHz, DMSO): 161.00, 159.17, 157.12, 149.72, 145.43, 138.12, 134.96, 133.31, 122.33, 120.00, 116.42, 114.15?ppm. HRMS determined for C14H10N2O3 254.07 found 254.06. (18). Produce (%) = 89. 1H NMR (500?MHz, DMSO): 13.12 (bs, 1H), 12.15 (s, 1H), 11.06 (bs, 1H), 8.22 (d, (19). Produce (%) = 83. 1H NMR (500?MHz, DMSO): 12.34 (s, 1H), 10.03 (bs, 1H), 8.03 (d, (20). Produce (%) = 82. 1H NMR (500?MHz, DMSO): 11.98 (s, 1H) 8.25 (d, (21). Produce (%) = 92. 1H L-655708 NMR (500?MHz, DMSO): 12.21 (s, 1H), 8.13 (d, (14), (22), and (23) (14). 2-amino-5-chlorobenzamide (0.7?mmol) and 3,4-dihydroxybenzaldehyde (0.91?mmol) were dissolved in an assortment of dichloromethane (10?ml) and acetonitrile (7?ml) and refluxed for 40?h. After conclusion, the solvent was eliminated under vacuum. The solid residue was treated with drinking water, filtered and washed once again with water to provide compound 14 like a pale yellowish crystal. Produce (%) = 82. 1H NMR (500?MHz, DMSO): 9.42 (s, 1H), 8.47 (bs, 1H), 8.38 (bs, 1H), 7.99 (s, 1H), 7.85 (d, (22). To an assortment of (3,4-dimethoxyphenyl)boronic acidity (3.29?mmol), K2CO3 (3.29?mmol), and Pd(OAc)2 (0.027?mmol) in ethanol (9?ml) and drinking water (3?ml) was slowly added 2-bromoquinoline (2.74?mmol). The blend was stirred at space temp for 18?h. Towards the ensuing blend was added drinking water (50?ml), and extracted with dichloromethane..1H NMR (500?MHz, DMSO): 9.42 (s, 1H), 8.47 (bs, 1H), 8.38 (bs, 1H), 7.99 (s, 1H), 7.85 (d, (22). 9.56 (bs, 1H), 9.23 (bs, 1H), 7.65 (s, 1H), 7.61 (d, (5). Produce (%) = 74. 1H NMR (500?MHz, DMSO): 12.07 (s, 1H), 9.60 (bs, 1H), 9.19 (bs, 1H), 7.63 (s, 1H), 7.50 (d, (6). Produce (%) = 77. 1H NMR (500?MHz, DMSO): 12.35 (s, 1H), 9.69 (bs, 1H), 9.29 (bs, 1H), 8.37 (s, 1H), 8.07 (d, (7). Produce (%) = 80. 1H NMR (500?MHz, DMSO): 12.02 (s, 1H), 9.52 (bs, 1H), 9.23 (bs, 1H), 8.43 (d, (8). Produce (%) = 87. 1H NMR (500?MHz, DMSO): 11.56 (s, 1H), 9.45 (bs, 1H), 9.27 (bs, 1H), 8.35 (s, 1H), 8.03 (d, J?=?8.0?Hz, 1H), L-655708 7.67(d, J?=?8.0?Hz, 1H), 7.13 (s, 1H), 6.83 (d, J?=?7.0?Hz, 1H), 6.78 (d, J?=?7.0?Hz, 1H) ppm. 13?C NMR (500?MHz, DMSO): 162.00, 160.54,154.27, 147.12, 146.04, 145.76,138.59, 134.73, 127.17, 122.22, 119.19, 116.15, 110.90?ppm. HRMS determined for C14H9IN2O3 379.97, found 379.97. (9). Produce (%) = 79. 1H NMR (500?MHz, DMSO): 12.11 (s, 1H), 9.56 (bs, 1H), 9.33 (bs, 1H), 8.15 (s, 1H), 7.98 (d, (10). Produce (%) = 90. 1H NMR (500?MHz, DMSO): 12.34 (s, 1H), 9.47 (bs, 1H), 9.38 (bs, 1H), 8.02(s, 1H), 7.78 (d, (11). Produce (%) = 87. 1H NMR (500?MHz, DMSO): 12.45 (s, 1H), 9.82 (bs, 1H), 9.42 (bs, 1H), 8.20 (d, (12). Produce (%) = 93. 1H NMR (500?MHz, DMSO): 12.46 (s, 1H), 9.76 (bs, 1H), 9.39 (bs, 1H), 7.88 (d, (13). Produce (%) = 84. 1H NMR (500?MHz, DMSO): 12.66 (s, 1H), 9.49 (bs, 1H), 8.78 (bs, 1H), 8.42 (d, (15). Produce (%) = 91. 1H NMR (500?MHz, DMSO): 12.73 (s, 1H), 9.65 (bs, 1H), 9.31 (bs, 1H), 8.08 (d, (16). Produce (%) = 81. 1H NMR (500?MHz, DMSO): 12.45 (s, 1H), 9.57 (bs, 1H), 9.01 (bs, 1H), 8.77 (d, (17). Produce (%) = 93. 1H NMR (500?MHz, DMSO): 12.20 (s, 1H), 9.63 (bs, 1H), 9.28 (bs, 1H), 8.11 (d, J?=?9.0?Hz, 1H), 7.79 (d, J?=?9.0?Hz, 1H), 7.67(s, 1H), 7.65 (t, J?=?9.0?Hz, 2H), 7.43 (d, J?=?8.0?Hz, 1H), 6.85 (d, J?=?9.0?Hz, 1H), ppm. 13?C NMR (500?MHz, DMSO): 161.00, 159.17, 157.12, 149.72, 145.43, 138.12, 134.96, 133.31, 122.33, 120.00, 116.42, 114.15?ppm. HRMS determined for C14H10N2O3 254.07 found 254.06. (18). Produce (%) = 89. 1H NMR (500?MHz, DMSO): 13.12 (bs, 1H), 12.15 (s, 1H), 11.06 (bs, 1H), 8.22 (d, (19). Produce (%) = 83. 1H NMR (500?MHz, DMSO): 12.34 (s, 1H), 10.03 (bs, 1H), 8.03 (d, (20). Produce (%) = 82. 1H NMR (500?MHz, DMSO): 11.98 (s, 1H) 8.25 (d, (21). Produce (%) = 92. 1H NMR (500?MHz, DMSO): 12.21 (s, 1H), 8.13 (d, (14), (22), and (23) (14). 2-amino-5-chlorobenzamide (0.7?mmol) and 3,4-dihydroxybenzaldehyde (0.91?mmol) were dissolved in an assortment of dichloromethane (10?ml) and acetonitrile (7?ml) and refluxed for 40?h. After conclusion, the solvent was eliminated under vacuum. The solid residue was treated with drinking water, filtered and washed once again with water to provide compound 14 like a pale yellowish crystal. Produce (%) = 82. 1H NMR (500?MHz, DMSO): 9.42 (s, 1H), 8.47 (bs, 1H), 8.38 (bs, 1H), 7.99 (s, 1H), 7.85 (d, (22). To an assortment of (3,4-dimethoxyphenyl)boronic acidity (3.29?mmol), K2CO3 (3.29?mmol), and Pd(OAc)2 (0.027?mmol) in ethanol (9?ml) and drinking water (3?ml) was slowly added 2-bromoquinoline (2.74?mmol). The blend was stirred at space temp for 18?h. Towards the ensuing blend was added drinking water (50?ml), and extracted with dichloromethane. The organic stage was separated, dried out over Mg2Thus4 and focused under decreased pressure to provide a good residue that was purified.