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Structure of 634905-12-7

Chemical Structure| 634905-12-7

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Product Details of [ 634905-12-7 ]

CAS No. :634905-12-7
Formula : C10H10BrNO2
M.W : 256.10
SMILES Code : O=C1N(C2=CC=C(Br)C=C2)CCOC1
MDL No. :MFCD11040374
InChI Key :SZMBYXUOLCRIIL-UHFFFAOYSA-N
Pubchem ID :17982707

Safety of [ 634905-12-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 634905-12-7 ]

* 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.

  • Downstream synthetic route of [ 634905-12-7 ]

[ 634905-12-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 109-11-5 ]
  • [ 106-37-6 ]
  • [ 634905-12-7 ]
YieldReaction ConditionsOperation in experiment
67.6% With dipotassium hydrogenphosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 105℃; for 15h;Inert atmosphere; Sealed tube; Example 144-(((lR,3S)-3-amino-2,2,3-trimethylcyclopentyl)amino)-6-(4-(3-oxo-4- morpholinyl)phenyl)pyrrolo [ 1 ,2-b]pyridazine-3 -carboxamide Step 1 : 4-(4-brom henyl)<strong>[109-11-5]morpholin-3-one</strong>[00234] A solution of 1,4-dibromobenzene (283 mg, 1.200 mmol), morpholin-3- one (101 mg, 1 mmol), dibasic potassium phosphate (348 mg, 2 mmol), copper (I) iodide (38.1 mg, 0.20 mmol) and N,N'-dimethylethylenediamine (0.043 ml, 0.40 mmol) in dioxane (3 ml) was purged with nitrogen for 2 min, sealed in a reaction vial and heated in a heating block at 105 C for 15 h. The crude product mixture was filtered, and charged to a 12 g silica gel cartridge which was eluted with 0-50% EtOAc in hexanes to give the title compound (173 mg, 0.676 mmol, 67.6 % yield) as a white solid. XH NMR (400 MHz, CDC13) δ ppm 10.56 (1 H, none), 7.55 (2 H, d, J=8.80 Hz), 7.24 (2 H, d, J=8.58 Hz), 4.04 (2 H, dd, J=5.83, 4.29 Hz), 3.73-3.79 (2 H, m). HPLC (condition G): ret. time 2.213 min. LC/MS [m/z, (M+H)] 258.0.
  • 2
  • [ 109-11-5 ]
  • [ 589-87-7 ]
  • [ 634905-12-7 ]
YieldReaction ConditionsOperation in experiment
80% With caesium carbonate; at 120℃; for 14h;Schlenk technique; Inert atmosphere; General procedure: The aryl iodide (1.5 mmol), amide (1 mmol), Cesium carbonate(1.5 mmol, 489 mg), and Cu/C (50 mg) were weighted into a Schlenk flask (10 mL) with a small magnetic stir bar. The reaction flask was evacuated and backfilled with nitrogen three times, and butyrylonitrile (3 ml) was added by syringe under nitrogen atmosphere. The resulting mixture was sealed under nitrogen and heated at 120 C for 14 h. The reaction mixture was cooled to room temperature, filtered, and the solvent removed by reduced pressure distillation. The residue was purified by silica gel flash chromatography to get the product.
60% With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine; In toluene; for 6h;Reflux; A mixture of 4-bromoiodobenzene (1.10 g, 3.77 mmol), <strong>[109-11-5]morpholin-3-one</strong> (0.58 g, 5.74 mmol), potassium carbonate (1.05 g, 7.52 mmol), cuprous iodide (72 mg, 0.38 mmol), N1,N2-dimethylethane-1,2-diamine (68 mg, 0.76 mmol) and anhydrous toluene (20 mL) in a 50 mL two-neck flask was refluxed for 6 h. The reaction mixture was cooled to rt, and added dropwise into ice-water. The mixture was stirred, and extracted with ethyl acetate (50 mL*3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to remove the solvent. The residue was purified by silica-gel column chromatography (EtOAc:DCM=1:7, V/V) to give a white solid (0.58 g, 60%). MS (ESI, pos.ion) m/z:257.01(M+2);
210 mg With copper(l) iodide; N,N`-dimethylethylenediamine; In water; N,N-dimethyl-formamide; at 100℃; for 0.5h;Inert atmosphere; Microwave irradiation; A) 4-(4-bromophenyl)<strong>[109-11-5]morpholin-3-one</strong> [1027] To a mixture of <strong>[109-11-5]morpholin-3-one</strong> (100 mg), 1-bromo-4-iodobenzene (282 mg), cesium carbonate (326 mg) and N1,N2-dimethylethane-1,2-diamine (9 mg) in DMF (2 mL) was added copper(I) iodide (10 mg) at room temperature under nitrogen atmosphere. The reaction mixture was stirred under microwave irradiation at 100C for 30 min. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (210 mg). MS (ESI+): [M+H]+ 256.0. MS (ESI+), found: 256.0.
  • 3
  • [ 29518-11-4 ]
  • [ 634905-12-7 ]
 

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