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Chemical Structure| 1061357-86-5 Chemical Structure| 1061357-86-5

Structure of 1061357-86-5

Chemical Structure| 1061357-86-5

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Product Details of [ 1061357-86-5 ]

CAS No. :1061357-86-5
Formula : C5H2Br2IN
M.W : 362.79
SMILES Code : IC1=CC(Br)=NC=C1Br
English Name :2,5-Dibromo-4-iodopyridine
MDL No. :MFCD13181646
InChI Key :JHAWIJLEDSUTBA-UHFFFAOYSA-N
Pubchem ID :58155015

Safety of [ 1061357-86-5 ]

Application In Synthesis of [ 1061357-86-5 ]

* 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 [ 1061357-86-5 ]

[ 1061357-86-5 ] Synthesis Path-Downstream   1~10

  • 2
  • [ 624-28-2 ]
  • [ 1061357-86-5 ]
  • [ 1353056-38-8 ]
  • [ 1214383-63-7 ]
  • [ 1353056-39-9 ]
  • [ 1353056-40-2 ]
YieldReaction ConditionsOperation in experiment
1: 46 %Spectr. 2: 23 %Spectr. 3: 8 %Spectr. 4: 4 %Spectr. 5: 2 %Spectr. Stage #1: 2,5-dibromo-pyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; ZnCl2(tmeda) In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran Inert atmosphere; regioselective reaction;
  • 3
  • [ 1061357-86-5 ]
  • [ 16135-36-7 ]
  • [ 1801334-97-3 ]
YieldReaction ConditionsOperation in experiment
1.51 g With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 0.75h; Inert atmosphere; 1.2 SyntSynthesis of methyl 4-[(2,5-dibromo-4-pyridyl)amino]pyridine-3-carboxylatehesis of methyl 4-[(2,5-dibromo-4-pyridyl)amino]pyridine-3-carboxylate To a suspension of 2,5-dibromo-4-iodo-pyridine (3.5 g, 0.0096 mol) methyl 4- aminopyridine-3-carboxylate (1.615 g, 0.0106 mol) and potassium phosphate tribasic (4.095 g, 0.0193 mol) in dioxane (20 mL) was purged with nitrogen for 45 min at RT. Then, to this reaction mixture was added Xantphos (0.837 g, 0.00144 mol) and Pd2(dba)3 (1.397 g, 0.00144 mol) and purging with nitrogen was continued for 10 min. The reaction mixture was heated at 110 °C overnight. The progress of reaction was monitored by TLC and LCMS. After completion of reaction, the mixture was filtered through a celite bed and the celite bed was washed with EtOAc. The filtrate was concentrated under reduced pressure to obtain crude compound that was purified by column chromatography on silica (100:200 mesh) using 40% EtOAc-hexane system as eluent to afford methyl 4-[(2,5-dibromo-4-pyridyl)amino]pyridine-3- carboxylate pure compound (1.510 g) as a yellow solid.
  • 4
  • [ 1061357-86-5 ]
  • [ 1801334-98-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 0.75 h / 110 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene / 100 °C / Inert atmosphere
  • 5
  • [ 1061357-86-5 ]
  • [ 1801334-99-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 0.75 h / 110 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene / 100 °C / Inert atmosphere 3: water; sodium hydroxide / methanol / 1 h / 80 °C
  • 6
  • [ 1061357-86-5 ]
  • [ 1801333-16-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 0.75 h / 110 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene / 100 °C / Inert atmosphere 3.1: water; sodium hydroxide / methanol / 1 h / 80 °C 4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere 4.2: 35 °C / Inert atmosphere
  • 7
  • [ 624-28-2 ]
  • [ 1061357-86-5 ]
YieldReaction ConditionsOperation in experiment
7.3 g Stage #1: 2,5-dibromopyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -70℃; for 4h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -70℃; for 0.5h; 1.1 Synthesis of 2,5-dibromo-4-iodo-pyridine To a solution of diisopropylamine (3.24 mL, 0.023 mol) in anhydrous THF (50 mL) was added a 2M solution of n-BuLi in n-hexane (11.6 mL, 0.023 mol) at -70 °C under nitrogen atmosphere. The reaction mixture was stirred at -70 °C for 30 min. To this reaction mixture was added 2,5-dibromopyridine (5 g, 0.021 mol) in THF (30 mL) dropwise. The reaction mixture was stirred at -70 °C for 4 h. To the reaction mixture, then was added a solution of iodine (6.96 g, 0.0274 mol) in THF (20 mL) and stirred for 30 min at the same temperature. The progress of reaction was monitored by TLC & 1H NMR. After completion of reaction, the mixture was quenched using aqueous Sodium thiosulfate solution and the product was extracted with EtOAc. The organic layer was washed with aqueous sodium thiosulfate solution and brine solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2,5-dibromo-4-iodo-pyridine (7.3 g) as a yellow solid pure compound
2.25 g Stage #1: 2,5-dibromopyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: With iodine In tetrahydrofuran for 0.5h; 2,5-Dibromo-4-iodopyridine (8a). To LDA (7.85 mmol) in THF (5 mL) at -78 °C was added 6 (1.59 g, 6.33 mmol) in THF (5 mL) dropwise, and the reaction mixture was stirred for 10 minutes. Iodine (4.82 g, 18.99 mmol) in THF (10 mL) was added dropwise, and the mixture was stirred for 30 minutes. Saturated sodium bicarbonate was added and the mixture was extracted with ether. The combined extracts were washed with 10% sodium thiosulfate and brine, and dried over anhydrous magnesium sulfate. Concentration and purification by radial PLC (silica gel, EtOAc/hexane, 2:98) yielded 2.25 g (98%) of 8a as a white solid, mp 136-138 °C; 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 8.46 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 114.4, 128.4, 138.6, 140.1, 150.6; FTIR (film) 659, 765, 867, 1012, 1101, 1268, 1293, 1412, 1430, 1528, 2341, 2361, 3061, 3083 cm-1; HRMS (FAB) calcd for C5H2Br2IN (M+1) 361.7677; found 361.7697. Structure confirmed by X-ray crystallography.
  • 8
  • [ 1061357-86-5 ]
  • [ 2929326-17-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: copper(l) iodide / methanol / Reflux 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / Inert atmosphere 3.1: sodium tetrahydroborate; ethanol / dichloromethane / 0.5 h / 20 °C 4.1: sodium iodide; chloro-trimethyl-silane / acetonitrile / 1 h / Reflux
  • 9
  • [ 1061357-86-5 ]
  • [ 2929326-18-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: copper(l) iodide / methanol / Reflux 2.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.08 h / -78 °C 2.2: 0.5 h 2.3: 0.25 h / 20 °C
  • 10
  • [ 1061357-86-5 ]
  • [ 2929326-19-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: copper(l) iodide / methanol / Reflux 2.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 0.5 h
 

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