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Chemical Structure| 88511-27-7 Chemical Structure| 88511-27-7
Chemical Structure| 88511-27-7

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Synonyms: 3-Iodo-4-pyridinamine

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Product Details of 4-Amino-3-iodopyridine

CAS No. :88511-27-7
Formula : C5H5IN2
M.W : 220.01
SMILES Code : C1=CN=CC(=C1N)I
Synonyms :
3-Iodo-4-pyridinamine
MDL No. :MFCD02663853
InChI Key :ZGOCEDVVZKFHSY-UHFFFAOYSA-N
Pubchem ID :1516510

Safety of 4-Amino-3-iodopyridine

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H315-H318-H335
Precautionary Statements:P280-P301+P312+P330-P302+P352-P305+P351+P338+P310

Application In Synthesis of 4-Amino-3-iodopyridine

* 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 [ 88511-27-7 ]

[ 88511-27-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 88511-27-7 ]
  • [ 107-18-6 ]
  • [ 253-72-5 ]
  • 2
  • [ 88511-27-7 ]
  • [ 24424-99-5 ]
  • [ 211029-67-3 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; B. (3-Iodo-pyridin-4-yl)-carbamic acid tert-butyl ester Di-tert-butyl dicarbonate (20.7 g, 94.8 mmol) is added to a solution of 4-amino-3-iodo-pyridin (19.0 g, 86.4 mmol) in THF (86 mL). The resulting solution is stirred for 2 h at room temperature then concentrated to dryness. The residue is diluted with ethyl acetate and washed with saturated sodium bicarbonate solution and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The residue is purified by column chromatography eluding with 1% EtOAc/CH2Cl2 to give the title product and a small amount of the BOC-protected di-iodo compound. Trituration of the mixture with ether/hexane removes the undesired compound leaving the title product in the solution. Filtration of the solid and concentration of the filtrate yields the title product (18.95 g, 59.2 mmol). 1H NMR (CDCl3, 300 MHz) delta8.75(s, 1H), 8.35(d, 1H), 8.1(d, 1H), 7.0(bs, 1H), 1.55(s, 9H).
  • 3
  • [ 88511-27-7 ]
  • [ 24424-99-5 ]
  • C10H12I2N2O2 [ No CAS ]
  • [ 211029-67-3 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; for 2h; B. (3-Iodopyridin-4-yl)-carbamic acid tert-butyl ester. Di-tert-butyl dicarbonate (20.7 g, 94.8 mmol) is added to a solution of 3-iodopyridin-4-ylamine (19.0 g, 86.4 mmol) in THF (86 ML).The resulting solution is stirred for 2 hours at room temperature then concentrated.The residue is diluted with ethyl acetate and washed with saturated sodium bicarbonate solution and brine.The organic layer is dried over MgSO4, filtered and concentrated.The residue is purified by column chromatography eluding with 1% EtOAc/CH2Cl2 to give the title product and a small amount of the BOC-protected di-iodo compound.Trituration of the mixture with ether/hexane removes the undesired compound leaving the title product in the solution.Filtration of the solid and concentration of the filtrate yields the title product (18.95 g, 59.2 mmol).1H NMR (CDCl3, 300 MHz) delta8.75 (s, 1H), 8.35 (d, 1H), 8.1 (d, 1H), 7.0 (bs, 1H), 1.55 (s, 9H).
  • 4
  • [ 70298-89-4 ]
  • [ 88511-27-7 ]
YieldReaction ConditionsOperation in experiment
To a 0.5 M solution of 2,2-dimethyl-7V-pyridin-4-ylpropanamide inTHF at -78°C was added 2.2 equiv of n-BuLi [1.7M] over 5-10 min. After allowing the reaction to warmup to -25°C to -20°C and stirring at this temperature for Ih, this mixture was cooled again to -78° C andtreated with a 3.4 M solution of iodine in THF over 5 min. The reaction mixture was warmed to roomtemperature and poured into a separatory funnel containing aqueous Na2S2O3/EtOAc. The layers wereseparated and the aqueous layer was extracted again with EtOAc. The combined organic layer waswashed with Na2S2O3, brine, and was then dried over anhydrous Na2SO4, filtered and concentrated. A0.17 M solution of the resulting crude material in 10percent aqueous H2SO4 (v/v) was then refluxedovernight. After allowing the reaction to cool to room temperature, aqueous 5N NaOH was added untilthe solution was slightly basic as indicated by pH paper. The aqueous layer was extracted twice withEtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered andconcentrated. The crude material was further purified by a pad of silica gel by eluting with a gradient.from 50percent EtOAc/hexanes to 100percent EtOAc and the product was swished in Et2O/hexanes to yield thetitle compound as an off-white solid. IH NMR (acetone-de) 5 8.48 (IH, s), 8.02 (IH, d), 6.75 (IH, d),5.75 (2H, br s).
  • 5
  • [ 88511-27-7 ]
  • [ 148493-34-9 ]
  • 2',6'-dichloro-[3,3'-bipyridin]-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere; General procedure: Procedure A : Suzuki coupling To a solution of iodopyridine (1 eq) in dioxane (5 mL/mmol), the boronic acid (1.5 eq), and 1 M Na2C03 aqueous solution (3 eq) were added and the reaction mixture was degassed with argon for 20 min. Then Bis(triphenylphosphine)palladium(ll) dichloride (0.2 eq) was added and the reaction mixture was heated at 100C for 16h. After completion of reaction, the reaction mixture was filtered through a celite pad and the filtrate was concentrated under reduced pressure to afford a residue that was dissolved in water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to afford the crude product, which was further purified by silica gel (100:200 mesh) column chromatography to afford the Suzuki coupling product.
44% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere; To a solution of 3-iodopyridin-4-amine (6 g, 27.2 mmol) in dioxane (135 ml_), (2,6-dichloropyridin- 3-yl)boronic acid (7.29 g, 38.1 mmol), and 1 M Na2CC>3 aqueous solution (3 eq) were added and the reaction mixture was degassed with argon for 20 min. Then Bis(triphenylphosphine)palladium(ll) dichloride (3.79 g, 5.4 mmol) was added and the reaction mixture was heated at 100C for 16h. After completion of reaction, the reaction mixture was filtered through a celite pad and the filtrate was concentrated under reduced pressure to afford a residue that was dissolved in water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to afford the crude product, which was further purified by silica gel (100:200 mesh) column chromatography to afford 2',6'-dichloro-[3,3'-bipyridin]-4-amine (i1 ) (2.9 g, Yield 44%). (0139) 1H NMR (400 MHz, DMSO-de) delta 6.04 (s, 2H), 6.62 (d, J = 5.8 Hz, 1 H), 7.71 - 7.55 (m, 1 H), 7.94 - 7.75 (m, 2H), 8.03 (d, J = 5.7 Hz, 1 H). (0140) MS (ESI) m/e (M+1 )+: 240.05
44% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere; To a solution of 3-iodopyridin-4-amine (6 g, 27.2 mmol) in dioxane (135 mL), <strong>[148493-34-9](2,6-dichloropyridin-3-yl)boronic acid</strong> (7.29 g, 38.1 mmol), and 1M Na2CO3 aqueous solution (3 eq) were added andthe reaction mixture was degassed with argon for 20 mm. ThenBis(triphenylphosphine)palladium(ll) dichloride (3.79 g, 5.4 mmol) was added and the reactionmixture was heated at 100C for 16h. After completion of reaction, the reaction mixture wasfiltered through a celite pad and the filtrate was concentrated under reduced pressure to afford a residue that was dissolved in water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure to afford the crude product, which was further purified by silica gel (100:200 mesh) column chromatography toafford 2,6-dichloro-[3,3-bipyridin]-4-amine (ii) (2.9 g, Yield 44%).1H NMR (400 MHz, DMSO-d6) 66.04 (s, 2H), 6.62 (d, J= 5.8 Hz, 1H), 7.71 -7.55 (m, 1H), 7.94- 7.75 (m, 2H), 8.03 (d, J = 5.7 Hz, 1 H).MS (ESI) m/e (M+1): 240.05
  • 6
  • [ 88511-27-7 ]
  • [ 1015460-62-4 ]
 

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