6-Ethoxynaphthalen-2-yl boronic acid

4-[2-(Perfluorohexyl)ethylsulfanyl]bromobenzene (compound A) (1.24 g, 2.31 mmol), 6-ethoxy-2-naphthylbronic acid (0.50 g, 2.31 mmol), Na2CO3 (0.49 g, 4.63 mmol), Pd(OAc)2(0.01 g, 2 mol%), and tri(o-tolyl)phosphine (0.03 g, 4 mol%) were added in 1, 4-dioxane(40 mL) and water (40 mL) in a 200mL flask, and the mixture was refluxed for 12 h underN2 atmosphere. The reaction mixture was allowed to cool to room temperature. Then saturatedNaCl aqueous solution (100 mL) was added to the mixture, and the resulting solutionwas extracted with CHCl3 (100 mL × 3). The organic phases were combined and driedwith MgSO4, and after filtration, the filtrate was concentrated using a rotary evaporatorunder reduced pressure. The crude product was purified by silica gel column chromatography(eluent: CHCl3) and recrystallization (EtOH: toluene = 8: 2) to give compound 1-2 (1.26 g, 2.01 mmol) in 87% yield as colorless powder.: IR (KBr disc): nu = 2980, 2936, 1238-1211 cm-1, 1H NMR (500 MHz, CDCl3): delta = 1.50 (3H, t, J = 7.0 Hz), 2.40-2.50(2H, m), 3.12-3.15 (2H, m), 4.17 (2H, q, J = 6.7 Hz), 7.17 (1H, d, 2.4 Hz), 7.18 (1H, dd, J = 10.9, 2.4 Hz), 7.47 (2H, d, J = 8.5 Hz), 7.68 (2H, d, J = 8.5 Hz), 7.69 (1H, dd, J =10.9, 2.4 Hz), 7.79 (1H, d, J = 9.8 Hz), 7.81 (1H, d, J = 9.8 Hz), 7.97 (1H, d, J = 2.4 Hz)ppm.A mixture of A mixture of 1c (2.10 g, 5.0 mmol), General procedure: 3-Iodopyrazolopyrimidines or 3-bromopyrazolopyrimidines (1 equiv), Na2CO3 (2-4equiv), catalytic Pd(PPh3)4 (.05 equiv), and boronic acids or boronate pinacol esters (1-2 equiv)dissolved in a dimethoxyethane (1.5 ml) and water (0.5 ml) mixture were heated in a microwaveat 80 C for one hour. The reaction was then allowed to cooled to room temperature, diluted intoethyl acetate, washed with brine, dried with Na2SO4, filtered, and concentrated in vacuo. Thecrude product was then purified via flash chromatography over silica, eluting with either ahexanes/EtOAc or CH2Cl2/MeOH gradient. If necessary, further purification was performed withpreparatory RP-HPLC.

suzuki reaction

Molecular Weight:216.04
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:216.0957744
Monoisotopic Mass:216.0957744
Topological Polar Surface Area:49.7
Heavy Atom Count:16
Complexity:222
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes