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3-(5-(2,2'-bithiophen-5-yl)thiophen-2-yl)-6-(5-bromothiophen-2-yl)-2,5-di(2-ethylhexyl)pyrrolo[3,4-c]pyrrolo-1,4-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
45%
With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; potassium carbonate; In toluene; at 120℃; for 15h;
Compound 4 (2.85 mmol, 1.95 g) and compound 5 (2.04 mmol, 597 mg) in anhydroustoluene to dissolve that solution to K2CO3 (8.16 mmol, 1.13 g) and aliquat336 (0.15mmol%, trioctylmethylammonium chloride, Aldrich) was added was . To the reactionsolution was added Pd (PPh3) 4 (8 mol%) and refluxed at 120 C 15 hours. After thereaction, only the organic layer extracted with water and dichloromethane to thereaction solution and collecting the finished dried over magnesium sulphate andconcentrated. flash column chromatography (chloroform / hexane (2: 5)) separating thedesired compound by using a phosphorus compound to give a purple solid 6 of 700mg(yield 45%).
36%
With sodium carbonate; In toluene; at 90℃; for 24h;Inert atmosphere;
3,4-c] pyrrolo-1,4-dione 4.02 g (5.89 mmol) of 2,2 ', 3,6-bis (5-bromothienyl)-bithiophene-5-boronic acid pinacol ester (1.12 g, 3.84 mmol) and 15 ml of 1 M sodium carbonate in 100 mlAnd placed in a flask already filled with toluene. After the oxygen in the reaction mixture solution was removed using an argon bubble,The reaction was carried out in an argon atmosphere at 90 DEG C for 24 hours.The reaction solution was filtered through silica,Precipitated in methanol and then filtered to obtain a solid.The solid was purified by column chromatography using hexane / chloroform 1: 1 ratio solvent as a mobile phase to give a dark blue solid. The solids were again added to 300 ml of methanol and stirred, sonicated for 10 minutesAfter filtration, the solid was dried in a vacuum oven at 50 & lt; 0 & gt; C for 24 hours to give 1.05 g (36%) of a dark blue solid.
1.0042 g of the dibromo compound [1000623-95-9], 1.1079 g of the boronicacidester [479719-88-5], 0.0133 g of palladium(II)acetate and 0.0710 g of the phosphine ligand [672937-61-0] are dissolved under argon in 40 ml of degassed tetrahydrofurane in a reactor at reflux. Then 0.3700 g of LiOH monohydrate[1310-66-3] are added and the reaction mixture is refluxed for 20 hours. The reaction mixture is then poured on ice-water, filtered and washed with water. The dried filter cake is then purified by column chromatography over silica gel to give the compound of the formula A-1. 1H-NMR data (ppm, CDCl3): 8.95 2H d, 7.27 4H d, 7.21 4H dxd, 7.11 4H d, 7.04 4H d, 4.05 4H m, 1.95 2H m, 1.48-1.25 16H m, 0.95 6H t, 0.92 6H t.
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