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Chemical Structure| 14547-73-0 Chemical Structure| 14547-73-0

Structure of 14547-73-0

Chemical Structure| 14547-73-0

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Product Details of [ 14547-73-0 ]

CAS No. :14547-73-0
Formula : C12H9BrN2O
M.W : 277.12
SMILES Code : O=C(NC1=CC=C(Br)C=C1)C2=NC=CC=C2
MDL No. :MFCD00583419
InChI Key :RAJKUZRIZUSGKU-UHFFFAOYSA-N
Pubchem ID :836035

Safety of [ 14547-73-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 14547-73-0 ]

* 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 [ 14547-73-0 ]

[ 14547-73-0 ] Synthesis Path-Downstream   1~23

  • 2
  • [ 29745-44-6 ]
  • [ 106-40-1 ]
  • [ 14547-73-0 ]
YieldReaction ConditionsOperation in experiment
50% With triethylamine; In dichloromethane; at 0 - 20℃; for 3h; General procedure: To a 50 mL round bottom flask was charged with pyridine-2-carboxylic acid (369 mg, 3.0 mmol), then 20 mL DCM was added. The mixture was stirred at 0 C and then oxalyl chloride (0.5 ml, 6.0 mmol) was added dropwise. Afterwards, 4-5 drops of DMF was added and the mixture was allowed to warm to room temperature. After stirring for 4 hours, the DCM and excess oxalyl chloride was removed under vacuum to obtain crude acyl chloride. Then the crude acyl chloride was dissolved in 20 mL DCM and cooled to 0 C, Et3N (0.7 mL, 5.0 mmol) and aniline (2.4 mmol) was added, and then the mixture was allowed to warm to room temperature. After 3 hours, 20 mL of water was added to quench the reaction, and organic phase was separated. The aqueous phase was extract twice with 20 mL DCM. Organic phase was combined, and washed with 1 N HCl, saturated NaHCO3, and brine. Then the organic phase was dried over anhydrous Na2SO4, evaporated under reduced pressure. The crude product was purified by flash column chromatography to afford the 2-picolinamide.
  • 3
  • [ 110-91-8 ]
  • [ 14547-73-0 ]
  • N-(4-bromo-2-morpholinophenyl)picolinamide [ No CAS ]
  • 4
  • [ 98-98-6 ]
  • [ 106-40-1 ]
  • [ 14547-73-0 ]
YieldReaction ConditionsOperation in experiment
40% in a 1 L reaction flask, SOCl2 (thionyl dichloride) (100 mL) and 7a (36.9 g, 300mmol) were added successively. Under nitrogen protection, the reaction solution was stirred at 80 C for 4 hours,cooled and then concentrated. DCM (dichloromethane) (400 mL) was added, cooled to 10 C and Et3N (121.1 g,1200 mmol) was added slowly under nitrogen protection. The obtained system was cooled to 0 C, a solution of106-40-1 (p-bromoaniline) (51.6 g, 300 mmol) in DCM (100 mL) was added dropwise. The temperature was naturallyincreased to room temperature and the obtained system continued to react for 14 hours and was concentrated andseparated by rapid column chromatography to obtain intermediate 8 (33.39 g, yield: 40%) as a grey solid. LCMSshowed a molecular ion peak (M+1) 277.0.
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 12h;Schlenk technique; Inert atmosphere; General procedure: A 100 mL two-necked round-bottom flask was equipped with magnetic stir bar and charged with amine (20 mmol), picolinic acid (1.1 equiv), N,N-dimethyl-4-aminopyridine (DMAP, 0.1 equiv., 0.244 g) dissolved in 30 mL anhydrous CH2Cl2 at 0 . Then EDCI (4.2 g, 1.1 equiv.) in CH2Cl2 (20 mL) was dropwise added to the solution under a nitrogen atmosphere. After the addition, the reaction was then warmed to room temperature, stirred for 12h and quenched with water (30 mL). Then the reaction mixture was extracted with ethyl acetate (20 × 3 mL) and the combined organic solvent was dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography PE:EtOAc (15:1) to give pure amides.
  • 5
  • manganese(II) chloride tetrahydrate [ No CAS ]
  • [ 14547-73-0 ]
  • [MnCl2(N-(4-bromo)phenylpicolinamide)2] [ No CAS ]
  • 6
  • [ 5720-05-8 ]
  • [ 14547-73-0 ]
  • N-(4-bromophenyl)-N-(p-tolyl)picolinamide [ No CAS ]
  • 7
  • ruthenium(III) chloride trihydrate [ No CAS ]
  • [ 14547-73-0 ]
  • C24H18Br2Cl2N4O2Ru [ No CAS ]
  • 8
  • [ 2926-29-6 ]
  • [ 14547-73-0 ]
  • N-(4-bromo-2-(trifluoromethyl)phenyl)picolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With tetrabutylammonium tetrafluoroborate; In acetonitrile; at 50℃; for 2h;Electrolysis; Schlenk technique; General procedure: A mixture of 1 (0.3 mmol), 2a (1.5 eq.), n-Bu4NBF4 (0.3 eq.) in CH3CN (3 mL) was charged with a 10 mL three-necked round-bottomed flask which equipped with a magneton, a carbon anode (d = 6 mm, about 5 mm immersion depth in solution), and a platinum plate (5 mm × 5 mm × 0.3 mm) cathode. The reaction mixture was stirred and electrolyzed at a constant current of 15 mA at 50 C for 2 h. Then the mixture was cooled to room temperature, poured into H2O (10 mL) and extracted with ethyl acetate (10 × 3 mL). The combined organic solvent was dried over Na2SO4, filtered and concentrated under reduced pressure. The given residue was purified by column chromatography using PE:EtOAc (30:1) as an eluent to provide the desired product 3.
  • 9
  • [ 14547-73-0 ]
  • [ 445-02-3 ]
  • 10
  • [ 109-99-9 ]
  • [ 14547-73-0 ]
  • N-(4-bromophenyl)-N-(2-tetrahydrofuranyl)picolinamide [ No CAS ]
  • 12
  • [ 10354-53-7 ]
  • [ 14547-73-0 ]
YieldReaction ConditionsOperation in experiment
54% With N-Bromosuccinimide; [bis(acetoxy)iodo]benzene; copper(I) bromide; In N,N-dimethyl-formamide; at 60℃; for 3h; Add N-(phenyl)pyridine amide (39.62 mg, 0.2 mmol) into a 25 mL single-neck bottle, bromosuccinimide (83.49 mg, 0.48 mmol),Copper bromide (8.83 mg, 20 mol%), iodobenzene acetate (128.79 g, 2.0 eq), N,N-dimethylformamide (4 mL). Stir at 60C for 3.0h in an air atmosphere. Then the mixture was cooled to room temperature, after cooling and filtering, it was concentrated under reduced pressure. Purified by silica gel column chromatography (developing solvent: petroleum ether: ethyl acetate = 80:1), 29.81 mg of the white solid target product was obtained with a yield of 54%.
  • 13
  • [ 14547-73-0 ]
  • N-(2-nitro-4-bromophenyl) 2-pyridinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium persulfate; sodium nitrite; In 1,2-dichloro-ethane; at 20℃; for 1h;Green chemistry; General procedure: N-Aryl protected carboxamide (1, 0.5 mmol, 1.0 equiv.), NaNO2 (0.6 mmol, 1.2 equiv.) were transferred to DCE (2.5 mL) and then Na2S2O8 (1.0 mmol, 2.0 equiv.) were added to the mixture in one portion and the corresponding mixture was stirred for additional 1 h upon the completion of the reaction (monitored by TLC). The crude product was washed with DCM (3 20 mL) and combined. Then the organic solvent was removed by evaporation and the residue was purified by silica gel column chromatography with amixture of n-hexane, dichloromethane or ethyl acetate to afford the desired product in noted yields.
  • 14
  • [ 14547-73-0 ]
  • [ 875-51-4 ]
  • 15
  • [ 14547-73-0 ]
  • C30H27N7O3 [ No CAS ]
  • 16
  • [ 14547-73-0 ]
  • C22H21N7O [ No CAS ]
  • 17
  • [ 14547-73-0 ]
  • C26H23N7O2 [ No CAS ]
  • 18
  • [ 14547-73-0 ]
  • [ 73183-34-3 ]
  • N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)picolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 14h;Inert atmosphere; in a 1 L reaction flask, intermediate 8 (13.8 g, 50 mmol), bis(pinacolato)diboron(13.97 g, 55 mmol), KOAc (potassium acetate) (14.7 g, 150 mmol), Pd(dppf)Cl2 ([1,1’-bis(diphenylphosphino)ferrocene]dichloropalladium) (1.5 g) and dioxane (250 mL) were added successively. The reaction solution was reactedat 100 C for 14 hours under argon protection. The reaction solution was cooled, then concentrated and separatedby rapid column chromatography to obtain intermediate 9 (10.93 g, yield: 68%) as a white solid. LCMS showed amolecular ion peak (M+1) 325.0.
  • 19
  • [ 5765-65-1 ]
  • [ 14547-73-0 ]
  • N-(4-bromo-2-morpholinophenyl)picolinamide [ No CAS ]
  • 20
  • [ 677-25-8 ]
  • [ 14547-73-0 ]
  • 6-(4-bromophenyl)-5-methylene-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one [ No CAS ]
  • 21
  • 1-morpholino-1,2-benzo[d]iodaoxol-3-(1H)-one [ No CAS ]
  • [ 14547-73-0 ]
  • N-(4-bromo-2-morpholinophenyl)picolinamide [ No CAS ]
  • 22
  • [ 14547-73-0 ]
  • N-(2-amino-4-bromophenyl)picolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% General procedure: A solution of 2-picolinamide 1a-1z (0.1 mmol, 1.0 eq.) and CuCl (0.15 mmol, 1.5 eq.) in dry toluene (3 mL) was added benzophenone imine (0.25 mmol, 2.5 eq.) in 10 ml sealed vials under air. The mixture was stirred at 80 C in oil bath for 16 hours. Then the mixture was diluted with EA (20 mL) and washed twice with aqueous solution of ammonia (10 mL), followed by brine (10 mL). The organic phase was evaporated, then diluted with 2 N HCl : THF 1:1 (4 mL) and stirring under 30 C for 3-12 hours. Saturated NaHCO3 was added and then the mixture was extract with EA three times. The organic phase was washed with brine and dried over anhydrous Na2SO4. Then the organic solvent was evaporated under reduced pressure to give the crude product, which was further purified by flash column chromatography to afford 3a-3z
  • 23
  • [ 110-05-4 ]
  • [ 14547-73-0 ]
  • N-(4-bromo-2-(tert-butoxy)phenyl)picolinamide [ No CAS ]
 

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Technical Information

Categories

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Related Parent Nucleus of
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