Tri-tert-butylphosphine tetrafluoroborate

Under inert gas protection, Tri-tert-butylphosphonium tetrafluoroborate (9.3 g, 0.032 mil, 4Eq), tris (dibenzylideneacetone) dipalladium () chloroform adduct (8. 3g, 008 mol, leq) and 200 mlDimethyl sulfoxide was added to the reaction flask, And then slowly dropping to them1M sodium methoxide solution in methanol(32L, 0.032, 0e, 4eq), 50 ° C for 15 h.Gloves bag filter, The filter cake was washed with dimethyl sulfoxideThe The filter cake was dried in n-hexane.filter, The filtrate was concentrated and crystallized.filter, The filter cake was washed with a small amount of n-hexane and the filter cake was washed with a small amount of n-hexane and dried to give 3. 27 g of a white solid powder in 80percent yield, elemental analysis: C, 56.17;H, 10. 50; P, 12. 07; Pd, 21.26Under inert gas protection, Tri-tert-butylphosphonium tetrafluoroborate (9.3 g, 0.032 mil, 4Eq), tris (dibenzylideneacetone) dipalladium () chloroform adduct (8. 3g, 008 mol, leq) and 200 mlDimethyl sulfoxide was added to the reaction flask, And then slowly dropping to them1M sodium methoxide solution in methanol(32L, 0.032, 0e, 4eq), 50 ° C for 15 h.Gloves bag filter, The filter cake was washed with dimethyl sulfoxideThe The filter cake was dried in n-hexane.filter, The filtrate was concentrated and crystallized.filter, The filter cake was washed with a small amount of n-hexane and the filter cake was washed with a small amount of n-hexane and dried to give 3. 27 g of a white solid powder in 80percent yield, elemental analysis: C, 56.17;H, 10. 50; P, 12. 07; Pd, 21.26Example 33 Preparation of methyl 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1, 2, 4-triazol-3-yl)phenyl)acetate (C17) In a 200 mL flask, 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1, 2, 4-triazole (3.45 g, 11.2 mmol), and methyl 2-(4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)phenyl)acetate (3.71 g, 13.4 mmol) were diluted with dioxane (45 mL) and water (11 mL). This solution was sparged with nitrogen gas for 10 minutes. Then tri-tert-butylphosphonium tetrafluoroborate (0.325 g, 1.12 mmol), diacetoxypalladium (0.126 g, 0.560 mmol) and cesium fluoride (3.40 g, 22.4 mmol) were added as solids. The flask was sealed and evacuated with vacuum and purged with nitrogen gas. The reaction was warmed to an internal temperature of 60° C. and stirred for 18 hours. The reaction was poured into a brine solution and extracted with ethyl acetate (3*50 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated. The resulting residue was purified by flash chromatography using 0-10percent ethyl acetate/hexanes as eluent to afford the title compound as an off white solid (3.45 g, 82percent): 1H NMR (400 MHz, DMSO-d6) delta 9.41 (s, 1H), 8.11-8.04 (m, 4H), 7.63 (ddt, J=7.9, 2.1, 1.1 Hz, 2H), 7.48-7.36 (m, 2H), 3.77 (s, 2H), 3.64 (s, 3H); 19F NMR (376 MHz, DMSO-d6) delta -57.02; ESIMS m/z 378 ([M+H]+)(4'-Chloro-3'-fluoro-4-methylbiphenyl-3-yl)acetic acid Under argon, 33.5 g (192 mmol) of (4-chloro-3-fluorophenyl)boronic acid were added to a solution of 40.0 g (175 mmol) of (5-bromo-2-methylphenyl)acetic acid (EP 1791816 and WO 2006/29799) in a mixture of 437 ml (437 mmol) of degassed 1N aqueous sodium hydroxide solution, 160 ml of degassed water and 160 ml of degassed tetrahydrofuran. The mixture was stirred for 10 minutes, 507 mg (1.75 mmol) of tri-tert-butylphosphonium tetrafluoroborate and 532 mg (1.75 mmol) of palladium(II) acetylacetonate were added and the mixture was stirred at room temperature for 20 h. Toluene and water were then added, the pH was adjusted to 1-2 with concentrated aqueous hydrogen chloride solution, the mixture was stirred for 10 minutes, the phases were separated, the aqueous phase was extracted twice with toluene and the combined organic phases were dried over sodium sulphate, filtered and concentrated. The residue was stirred in 300 ml of a 6/1 mixture of n-hexane/tert-butyl methyl ether for 30 minutes, filtered off with suction, washed with n-hexane and dried under reduced pressure. This gave 38.0 g (78percent of theory) of the title compound. 1H NMR (300 MHz, DMSO-d6): delta [ppm]=2.27 (s, 3H), 3.67 (s, 2H), 7.27 (d, 1H), 7.49-7.59 (m, 3H), 7.61-7.75 (m, 2H), 12.4 (s, 1H). LC-MS (Method 1): Rt=1.31 min; MS (ESIneg): m/z=277 [M-H]-.

suzuki reaction

Molecular Weight:290.13
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:290.1957807
Monoisotopic Mass:290.1957807
Heavy Atom Count:18
Complexity:147
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes