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General procedure: Into a one-necked 25 mL flask, tricarballylic acid (518 mg, 2.95 mmol, 1.0 equiv) and the appropriate anhydride (8.83 mmol, 3 equiv) were suspended in m-xylene (5 mL, 0.6 M). Pyridine was added (47 muL, 0.59 mmol, 0.2 equiv) in one portion, then the mixture was heated to 140 C and stirred until the completion of the reaction was indicated by GC-MS (5-21 h). After cooling to r.t., CH2Cl2 (100 mL) was added and the mixture was passed through a short pad of Celite to remove insoluble side-products. The solution was washed with saturated Na2CO3 solution (2 10 mL) then with brine (10 mL). The organic phase was dried over Na2SO4, filtered, and evaporated to dryness. Purification by flash chromatography (hexanes/EtOAc) afforded the pure Fittig lactone.
In 1-methyl-pyrrolidin-2-one; water; at 445℃; under 187519.0 Torr; for 0.00277778h;Supercritical conditions;
Under the same conditions as in Example 1-5 except that N-methyl-1,2-phenylenediamine (manufactured by Sigma-Aldrich) and benzoic acid hydride (manufactured by Tokyo Chemical Industry Co., Ltd.) were used at a pressure of 25 MPa, (13) was carried out in supercritical water. As a result, the reaction time was 10 seconds, and the yield was 99percent
Add 19g of diboron trioxide to a 1L three-neck bottle,181g benzoic acidAnd 439g benzoic anhydride,Mechanical stirring,Heating reaction (200±5C) reaction for 5h,After the reaction is over,Cool down to 5090C,Add 150 g of ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate,After continuing to heat the reaction (200±5C) for 4 hours,Thin layer chromatography was monitored until the reaction was completed (developer: ethyl acetate:methanol=20:1, UV 254 nm; the disappearance of the starting material indicates complete reaction).After the reaction was completed, the reaction solution was cooled to room temperature (10 to 30 C.), and the cooled material solution was placed in a refrigerator. Crystallization was continued for 12 hours (0 to 5 C.), and suction filtration was performed to obtain a brown-yellow solid, which was used as a filter cake. Anhydrous ethanol (0 ± 5 C) was beaten and washed three times, and suction filtration was continued until dry. The filter cake was laid flat on a watch glass and placed in a drying oven at 50 ± 5 C for 5 hours.Received, obtained 237g light yellow solid, yield 93.2%, namely 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinoline The carboxylic acid-O3,O4-dibenzoic acid boron (compound III) was used in the next step without purification.
tert-butyl (E)-3-(2-benzoyl-6-benzyl-4-(trifluoromethoxy)phenyl)acrylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
58%
With trifuran-2-yl-phosphane; norbornene; caesium carbonate; palladium dichloride; In 1,4-dioxane; at 90℃; for 12h;Sealed tube;
General procedure: Unless otherwise noted, in a glovebox, a 5.0 mL vial equipped with a Teflon coated stir bar was charged with PdCl2 (1.7 mg, 0.03mmol), P(2-furyl)3 (16.4 mg, 0.06 mmol), Cs2CO3 (391.0 mg,1.20 mmol), 1 (0.30 mmol), 2 (0.45 mmol), 3 (0.45 mmol), 4 (0.36 mmol) and NBE (56.5 mg, 0.6mmol) followed by sequential addition of 1,4-dioxane (3.0 mL). Next, the vial was sealed with a Teflon screw cap and removed from glovebox, and then, the mixture was allowed warm to 90 C refluxed for an additional 12 h. After completion of the reaction, the mixture was filtered through a thin pad of celite. The filter cake was washed with ethyl acetate (3 × 2.0 mL), then the combined filtrate was concentrated in vacuo to provide a crude reaction mixture that was purified by silica gel column chromatography to affored the desired product 5.
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