1-BOC-indole-3-boronic acid, pinacol ester

To a solution of (2-fluoro-4-iodophenyl) (1, 3, 3-trimethyl-6-azabicyclo[3.2.1]octan-6-yl)methanone (3c) (0.3 g, 0.75 mmol) andtert-butyl 3-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-1Hindole-1-carboxylate (4) (0.28 g, 0.82 mmol) in 1, 4-dioxane(4.0 mL) was added 1.0 mL of water. The reaction mixture wasdegassed with argon for about 30 min. After that Pd(dppf)Cl2.DCM(0.030 g, 0.037 mmol) and Na2CO3 (0.16 g, 1.50 mmol) were addedto the reaction mixture and again degassed with argon for another20 min The reaction mixture was stirred under reflux for 3 h. Aftercooled down to room temperature, the mixture was extracted withEtOAc, washed with brine, dried over Na2SO4, and concentratedunder reduced pressure. The crude product was purified by columnchromatography (Hexane/EtOAc 3:7) to afford 5c as a brown solid(0.31 g, 84.7%). 1H NMR (500 MHz, CDCl3) delta 8.26 (d, J 10.0 Hz, 1H), 7.81(s, 1H), 7.59e7.56 (m, 1H), 7.46e7.40 (m, 2H), 7.30 (d, J 10.0 Hz, 1H), 7.22 (d, J 10.0 Hz, 1H), 7.11e7.06 (m, 1H), 4.68 (s, 1H), 3.64 (d, J 10.0 Hz, 1H), 1.43e1.40 (m, 1H), 3.28 (d, J 5.0 Hz, 1H), 2.32e2.29 (m, 1H), 1.84e1.82 (m, 1H), 1.76e1.73 (m, 2H), 1.72 (s, 9H), 1.60 (s, 1H), 1.54e1.47 (m, 1H), 1.43e1.37 (m, 1H), 1.28 (s, 3H), 1.15 (s, 3H), 1.09 (d, J 10.0 Hz, 3H).To a solution of (3-hydroxy-4-iodophenyl) (1, 3, 3-trimethyl-6-aza-bicyclo[3.2.1]octan-6-yl)methanone (3b) (0.5 g, 1.25 mmol)and tert-butyl 3-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-1Hindole-1-carboxylate (4) (0.47 g, 1.38 mmol) in 1, 4-dioxane(10.0 mL) was added 2.0 mL of water. The reaction mixture wasdegassed with argon for about 30 min. After that Pd(dppf)Cl2.DCM(0.05 g, 0.063 mmol) and Na2CO3 (0.26 g, 2.50 mmol) were added tothe reaction mixture and again degassed with argon for another20 min The reaction mixture was stirred under reflux for 3 h. Aftercooled down to room temperature, the mixture was extracted withEtOAc, washed with brine, dried over Na2SO4, and concentratedunder reduced pressure. The crude product was purified by columnchromatography (Hexane/EtOAc 3:7) to afford 5b as a brownsolid (0.48 g, 78.5%). 1H NMR (500 MHz, CDCl3) delta 8.26 (d, J 10.0 Hz, 1H), 7.81(s, 1H), 7.59e7.56 (m, 1H), 7.46e7.40 (m, 2H), 7.30 (d, J 10.0 Hz, 1H), 7.22 (d, J 10.0 Hz, 1H), 7.11e7.06 (m, 1H), 4.68 (s, 1H), 3.64 (d, J 10.0 Hz, 1H), 3.43e3.40 (m, 1H), 3.28 (d, J 5.0 Hz, 1H), 2.32e2.29 (m, 1H), 1.84e1.82 (m, 1H), 1.76e1.73 (m, 2H), 1.72 (s, 9H), 1.60 (s, 1H), 1.54e1.47 (m, 1H), 1.43e1.37 (m, 1H), 1.28 (s, 3H), 1.15 (s, 3H), 1.09 (d, J 10.0 Hz, 3H).To a solution of (4-iodo-3-methoxyphenyl) (1, 3, 3-trimethyl-6-aza-bicyclo[3.2.1]octan-6-yl)methanone (3a) (0.3 g, 0.72 mmol)and tert-butyl 3-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-1Hindole-1-carboxylate (4) (0.27 g, 0.80 mmol) in 1, 4-dioxane(4.0 mL) was added 1.0 mL of water. The reaction mixture wasdegassed with argon for about 30 min. After that Pd(dppf)Cl2.DCM(0.03 g, 0.036 mmol) and Na2CO3 (0.15 g, 1.45 mmol) were added tothe reaction mixture and again degassed with argon for another20 min. The reaction mixture was stirred under reflux for 3 h. Aftercooled down to room temperature, the mixture was extracted withEtOAc, washed with brine, dried over Na2SO4, and concentratedunder reduced pressure. The crude product was purified by columnchromatography (Hexane/EtOAc 3:7) to afford 5a as a brownsolid (0.32 g, 87.9%). 1H NMR (500 MHz, CDCl3) delta 8.22 (d, J 10.0 Hz, 1H), 7.82 (s, 1H), 7.60 (d, J 5.0 Hz, 1H), 7.56 (d, J 5.0 Hz, 1H), 7.55e7.53 (m, 1H), 7.36 (s, 1H), 7.27 (d, J 5.0 Hz, 1H), 7.13 (d, J 10.0 Hz, 1H), 4.68 (s, 1H), 3.89 (s, 3H), 3.64 (d, J 10.0 Hz, 1H), 3.43e3.40 (m, 1H), 3.28 (d, J 5.0 Hz, 1H), 2.32e2.29 (m, 1H), 1.84e1.82 (m, 1H), 1.76e1.73 (m, 2H), 1.71 (s, 9H), 1.60 (s, 1H), 1.54e1.47 (m, 1H), 1.43e1.37 (m, 1H), 1.20 (s, 3H), 1.10 (s, 3H), 1.00(d, J 10.0 Hz, 3H).To a solution of methyl 4-iodo-3-methoxybenzoate (9) (0.5 g, 1.71 mmol) and

Molecular Weight:343.2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:343.1954885
Monoisotopic Mass:343.1954885
Topological Polar Surface Area:49.7
Heavy Atom Count:25
Complexity:512
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes