1-Ethyl 5-borono-2-chlorobenzoate

General procedure: To a solution of 9-bromonoscapine (200mg, 0.41mmol) in ethanol/toluene (1:1, v/v, 10mL) was added Pd(PPh3)4 (0.049mmol), sodium bicarbonate (0.82mmol) and 4a-g (0.82mmol), under nitrogen. Reaction mixture was heated at 120C for 48h, cooled to room temperature, solvents were removed under reduced pressure, water (10mL) was added, extracted with dichloromethane (3×25mL), and combined organic portions were washed with water, dried over anhydrous sodium sulphate and concentrated. Crude product was purified over silica gel column chromatography eluted with 25% ethyl acetate in hexanes to give pure compounds 5a-g as colorless solids.General procedure: In an oven dried round bottom flask, 9-bromonoscapine (0.2 g, 0.4072 mmol) in ethanol, toluene (10 mL, v/v, 1:1), aryl boronic acids 6a-6f (Fig. 5) (0.8145 mmol), Pd(PPh3)4 (0.04886 mmol) and sodium bicarbonate (0.8145 mmol) were added and heated at 120 C for 48 h. The reaction mixture was cooled to room temperature, solvents were removed under reduced pressure, water (10 mL) was added to the crude residue, then extracted with dichloromethane (3 9 25 mL), and combined organic portion was dried over anhydrous sodium sulphate and evaporated. The crude product was purified over silica gel column chromatography (25 % EtOAc in hexanes) to give pure compounds 5a-5f as white solids.Example 180 4, 3'-Dichloro-4'-[3, 3, 3-trifluoro-2-hydroxy-2-(6-methoxy-pyridin-3-yl)-1-methyl-propyl]-biphenyl-3-carboxylic acid ethyl ester In analogy to Example 150, step 2, 3-(4-bromo-2-chloro-phenyl)-1, 1, 1-trifluoro-2-(6-methoxy-pyridin-3-yl)-butan-2-ol (Example 175, step 3) was reacted with Example 170 4, 3'-Dichloro-4'-[3, 3, 3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1, 6-dihydro-pyridin-3-yl)-propyl]-biphenyl-3-carboxylic acid In analogy to Example 150, step 2, 5-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one (Example 165, step 3) was reacted with

suzuki reaction

Molecular Weight:228.44
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:228.0360667
Monoisotopic Mass:228.0360667
Topological Polar Surface Area:66.8
Heavy Atom Count:15
Complexity:224
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes