* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With potassium nitrite; copper(II) bis(trifluoromethanesulfonate); In dimethyl sulfoxide; at 135℃; for 60.0h;Inert atmosphere; Sealed tube;
General procedure: An oven dried pressure tube was charged with haloarenes (0.5 mmol), copper(II) triflate (45 mg, 0.125 mmol), KNO2 (128 mg, 1.5 mmol) and anhydrous DMSO (0.6 mL) under nitrogen atmosphere. The tube was sealed with a teflon screw cap having mininert valve and nitrogen is purged through it for 5 min. It is stirred at room temperature for 10 min and then the temperature was gradually increased to 130 oC and is maintained at the same for 48 h. The reaction mixture was then cooled to room temperature, washed with excess ice cold water and extracted with ethyl acetate (3 x 10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product which was purified by column chromatography using silica gel (Table 2, entries 1-18) or basic alumina (Table 2, entries 19-23) and a mixture of ethyl acetate and hexane as the eluent to afford the desired products in good yields.
With bis(tri-t-butylphosphine)palladium(0); dicyclohexylmethylamine; lithium chloride; In 1,4-dioxane; at 110℃; for 16h;Inert atmosphere;
General procedure: A flask containing LiCl (980 mg,23.1 mmol), 2-bromo-4-fluoroanisole (1.0 mL, 7.7 mmol), DCMA (1.8 mL,8.4 mmol) and <strong>[1001-26-9]ethyl 3-ethoxyacrylate</strong> (3.3 mL, 23 mmol) in 1,4-dioxane(20 mL) was degassed by passing a stream of nitrogen through the mixturefor 10 min. Bis(tri-t-butylphosphine) palladium(0) (166 mg, 0.32 mmol) wasadded, and reaction mixture was heated at reflux under nitrogen for 16 h. Thebrown mixture was then cooled and partitioned between ethyl acetate andwater. The layers were separated, and the organic layer was washedsequentially with aqueous NH4Cl and brine, followed by drying over Na2SO4.The mixture was filtered, and the filtrate was concentrated under reducedpressure to give an oil which was purified by flash chromatography on silica(40 g, 10?50percent ethyl acetate in heptane) to afford 22c as an orange oil (1.93 g,92percent) as an inseparable mixture of E- and Z-isomers: 1H NMR (CDCl3, 500 MHz)alkene protons d: 5.21, 5.33 ppm (1:1 ratio); LCMS (ES): 269.2 (MH). HRMSCalcd for C14H17FO: 269.1184. Found: 269.1196.
2,6-dimethoxy-2’-(methoxymethoxy)-1,1’-biphenyl[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
7.1 g
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; In toluene; at 110℃; for 12h;
Compound 5 (9.00 g, 49 mmol),Compound 23 (8.71 g, 33.0 mmol),Pd (dba) 2 (302 mg, 330 mmol),s-Phos (677 mg, 1.65 mmol),K3PO4 (13.2 g, 62.3 mmol) was weighed into a reaction vessel and toluene (50 ml) was added.This mixture was reacted at 110 C. for 12 hours to obtain a black suspension. H2O (50 ml) was added to the reaction solution, and extraction operation was performed with EtOAc (55 ml × 3).The organic layer was washed with saturated brine, dried over Na2SO4, filtered and the solvent was removed under reduced pressure.The resulting crude product was purified with a silica gel column to obtain 7.1 g of Compound 24 as a yellow oily substance.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
