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CAS No. : | 574-98-1 | MDL No. : | MFCD00005902 |
Formula : | C10H8BrNO2 | Boiling Point : | No data available |
Linear Structure Formula : | BrCH2CH2N(C(O))2C6H4 | InChI Key : | CHZXTOCAICMPQR-UHFFFAOYSA-N |
M.W : | 254.08 | Pubchem ID : | 11325 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With sodium carbonate; In dichloromethane; | b. A mixture of 69.3 g of <strong>[127561-18-6]1-[6-(trifluoromethyl)-2-pyridinyl]piperazine</strong>, and 129.6 g of N-(2-bromoethyl)phthalimide and 57.2 g of sodium carbonate is heated at reflux for 23 hours. The resulting precipitate is filtered off and the ethanol evaporated. The concentrate is dissolved in dichloromethane, washed with water, dried over magnesium sulfate, and evaporated. The resulting precipitate is recrystallized from isopropanol to give 39.5 g of 2-[2-[4-[6-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl]ethyl]-1H-isoindole-1,3-dione (yield 33%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h; | Step II: Preparation of 2-[2-(methylpyridin-4-ylmethylamino) ethylisoindole-l,3-dione; Potassium carbonate (55.2 mmol) and 2-bromoethylfthalimide (66.2 mmol) was added to a solution of N* l*-pyridin-4-yl-methylethane-l, 2-diamine (55.2 mmol) in EPO <DP n="82"/>dimethylformamide (50 mL). The reaction mixture was heated to 800C and stirred for about 16 hours. The reaction mixture was cooled to ambient temperature, poured into water and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield the title product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | In 1,4-dioxane; at 180℃; for 1h;Microwave irradiation; | Compound 42 (500 mg, 5.10 mmol) and N-(2-bromoethyl)-phthalimide (1.29 g, 5.58 mmol) were suspended in 1,4-dioxane (3 mL) in a microwave reaction vial containing a Teflon stir bar. The vial was capped and the reaction mixture was irradiated with microwaves at 180 C for 1 h at normal absorption with cooling activated. The reaction solvent was evaporated under vacuum, and the crude was purified by flash chromatography on silica gel using gradient 0-10% methanol in dichloromethane to afford product 43 (335 mg, 24%); 1H NMR (CDCl3) δ 1.98 (s, 3H), 3.10 (s, 2H), 3.94 (s, 4H), 7.68-7.70 (m, 2H), 7.80-7.82 (m, 2H). |
In 1,4-dioxane; at 180℃;Microwave irradiation; | Compound 42 (500 mg) and /V-(2-bromo ethyl)-phthalimide (1.3 g) were suspended in 1 ,4-dioxane (3mL) in a Biotage Initiator microwave reaction vial containing a Teflon stir bar. The vial was capped and the reaction mixture was transferred to the microwave and irradiated at 180 C at normal absorption with cooling activated. The reaction solvent was evaporated and the resulting crude was purified by flash chromatography on silica gel using gradient 0-10% MeOH-DCM to afford product 43. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With caesium carbonate; In acetonitrile; at 150℃; for 0.666667h;Microwave irradiation; | 1-[2-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)ethyl]-<strong>[35344-95-7]1H-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong></strong> In a 30-mL vial, <strong>[35344-95-7]1H-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong></strong> (2.0 g, 20.81 mmol, 1.00 equiv), 2-(2-bromoethyl)-2,3-dihydro-1H-isoindole-1,3-dione (6.3 g, 24.98 mmol, 1.20 equiv) and Cs2CO3 (13.5 g, 41.63 mmol, 2.00 equiv) were mixed in CH3CN (10 mL) at room temperature. The resulting mixture was irradiated with microwave for 40 min at 150° C. After the reaction was done, the reaction mixture was cooled to room temperature, diluted with 10 mL water and extracted with ethyl acetate (3*10 ml). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with ethyl acetate in petroleum ether (1percent to 50percent gradient) to afford 1-[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)ethyl]-<strong>[35344-95-7]1H-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong></strong> (800 mg, 14percent) as white solid. MS: m/z=270.0 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 24h; | <strong>[31191-08-9]5-hydroxy-2-pyridinecarboxaldehyde</strong> (1 eq.), N-(2-Bromoethyl)phthalimide (1 eq, 6.2 mmol) and K2CO3 (4 eq.) were dissolved in dry DMF (20 ml) and resulting mixture was heated at 70 C for 24 h. After evaporation of DMF, the residue was dissolved in CH2Cl2 and washed with water. The organic phase was collected and water phase was re-extracted two times with CH2Cl2. The organic phases was evaporated and the crude product purified by flash chromatography on silica (gradient of EtOAc : Petrol ether 1:4 to 2:1). The product was obtained as white solid in 63% yield. 1H-NMR (400MHz, CDCl3): 9.97 (s, 1 H); 8.40 (d, J = 2.7, 1 H); 7.93 (d, J = 8.8, 1 H); 7.89 (q, J = 2.8, 2 H); 7.75 (q, J = 2.8, 2 H); 7.30 (dd, J = 8.6, J = 2.6 , 1 H); 4.38 (t, J = 5.6, 2 H); 4.17 (t, J = 5.6, 2 H); 13C NMR (100MHz, CDCl3): 191.92, 168.04, 157.69, 146.70, 138.73, 134.28, 131.89, 123.54, 123.25, 120.80, 65.44, 36.88, ESI-MS: 297.0825, calc 297.0870 (M+H+) M.p.: 139-140C |
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